Manual (13) 2015

TABLE OF CONTENTS
CHEMISTRY 2231 LABORATORY SCHEDULE

LAB
PERIOD EXPERIMENT
PAGE
GENERAL INFORMATION ................................................................... 4
MELTING POINT ................................................................................ 12
RECRYSTALLIZATION ......................................................................... 16
DISTILLATION .................................................................................... 20
RESOLUTION OF RACEMIC PHENYLSUCCINIC ACID ............................. 23
SYNTHESIS OF TERTIARY BUTYL CHLORIDE......................................... 26
SYNTHESIS OF 2-METHYL-2-BUTENE .................................................. 29
SYNTHESIS OF 2,4,4-TRIMETHYL-2-PENTENE AND ISOMER ................. 32
9,10
OXIDATION OF CYCLOHEXENE TO ADIPIC ACID .................................. 35
11,12
SYNTHESIS OF 2-METHYL-4-HEPTANONE ........................................... 38

SYNTHESIS OF ETHYL IODIDE ............................................................. 43
13
CHECK OUT ....................................................................................... 46
14
ORGANIC POLYMERS ......................................................................... 47
TABLE OF CONTENTS
CHEMISTRY
2241 LABORATORY SCHEDULE
LAB
PERIOD EXPERIMENT
PAGE
GENERAL INFORMATION ................................................................... 4
COLUMN CHROMATOGRAPHY .......................................................... 52
SYNTHESIS OF 1,4-DI-T-BUTYL-2,5-DIMETHOXYBENZENE ................... 55
THE CANNIZZARO REACTION ............................................................. 58
PART I ............................................................................................... 59
PART II .............................................................................................. 59
PART III ............................................................................................. 60
SPECTROCOPY ................................................................................... 62
SYNTHESIS OF BENZOPHENONE OXIME ............................................. 67
THE REARRANGEMENT OF BENZIL ..................................................... 70
PREPARATION OF METHYL BENZOATE ............................................... 73
SYNTHESIS OF LIDOCAINE .................................................................. 77
Parts I & II ......................................................................................... 78
10
Part III ............................................................................................... 79
11
SYNTHESIS OF DIBENZALACETONE ..................................................... 85
12
-D-(+)-GLUCOSE PENTAACETATE ...................................................... 88
13
CHECK OUT ....................................................................................... 91
14
THE SYNTHESIS OF ASPIRIN ............................................................... 92
USEFUL INFORMATION
SAFETY ............................................................................................. 4
GRADING .......................................................................................... 5
LABORATORY NOTEBOOK ................................................................. 5
USING THE BALANCES ....................................................................... 6
HEATING IN THE LAB ......................................................................... 6
BUNSEN BURNERS ............................................................................ 7
DISTILLATION TECHNIQUE ................................................................. 7
REFLUX TECHNIQUE .......................................................................... 8
RECRYSTALLIZATION TECHNIQUE ...................................................... 8
FILTERING AND DRYING SOLID: ......................................................... 8
FILTER AID ........................................................................................ 9
DRYING ORGANIC LIQUIDS (THE REMOVAL OF WATER) ..................... 9
DRYING GLASSWARE......................................................................... 9
USES OF THE SEPARATORY FUNNEL: .................................................. 9
THEORETICAL YIELD .......................................................................... 10
PERCENTAGE YIELD ........................................................................... 11
HANDING IN PRODUCTS.................................................................... 11
Figure 1. Recrystallization technique (diagrammed). ......................... 95
Figure 2. Reflux Set-up. .................................................................... 96
Figure 3. Simple Distillation Set-up. .................................................. 97
Figure 4. Unpacked Column Distillation Set-up. ................................ 98
GENERAL INFORMATION
SAFETY
SAFETY IS THE NUMBER ONE PRIORITY. Always read and understand the
experiment before coming to lab. Follow the procedure and the directions of the
instructor exactly. If you do not understand what you doing, stop and ask the instructor.
Some of the laboratory rules and regulations are:
YOU MUST:
WEAR SAFETY GOGGLES AT ALL TIMES.
WEAR APPROPRIATE CLOTHING, NO SHORTS OR SANDALS.
WORK ONLY DURING SCHEDULED LAB PERIODS.
KNOW WHAT YOU ARE DOING AT ALL TIMES.
BE ALERT AT ALL TIMES.
NO MATTER HOW MINOR, REPORT ALL ACCIDENTS.
KNOW THE LOCATIONS OF THE SAFETY EQUIPMENT.
KEEP YOUR WORK SPACE AND THE HOODS CLEAN.
YOU MUST NOT:
EAT, DRINK, OR SMOKE IN THE LAB.
PERFORM UNAUTHORIZED EXPERIMENTS.
ACT IN A LOUD OR DISRUPTIVE MANNER.
REMOVE ANY CHEMICALS OR EQUIPMENT FROM THE LAB.
IN ADDITION:
CONTACT LENSES SHOULD NOT BE WORN IN THE LAB
DO NOT PUT ANY SOLIDS IN THE SINKS, THIS INCLUDES
BOILING CHIPS, RUBBER BANDS, AND BROKEN GLASS.
ALL IRONWARE AND HOSES MUST BE RETURNED TO THE SIDE
DRAWERS AFTER EACH LAB, IN THE CORRECT DRAWER.
DISCARD ALL CHEMICALS AS DIRECTED BY YOUR INSTRUCTOR.
VISITORS ARE NOT ALLOWED IN LAB.
DO NOT START AN EXPERIMENT OVER WITHOUT YOUR INSTRUCTOR'S
PERMISSION.
EACH STUDENT IS EXPECTED TO CONCENTRATE ON THEIR OWN
WORK AND NOT CARRY ON CONVERSATIONS WITH THEIR
4
NEIGHBORS. ANY QUESTIONS ARE TO BE DIRECTED TO THE

INSTRUCTOR.
IF A STUDENT HAS TO LEAVE THE LABORATORY FOR SOME
REASON, PERMISSION MUST BE OBTAINED FROM THE
INSTRUCTOR FIRST.
NEVER RETURN EXCESS CHEMICALS TO THE CONTAINER, PASS THEM
ON TO THE NEXT PERSON OR PROPERLY DISPOSE OF THEM. PUT TOPS
ON CONTAINERS IMMEDIATELY AFTER USE. THE TOPS ARE NOT USED
FOR ANYTHING ELSE, DON'T PUT CHEMICALS IN THEM.
STOP AND CLEAN UP IMMEDIATELY ANY SPILLAGE.
CLOSE THE ICE MACHINE DOOR AFTER YOU TAKE THE ICE.
SAFETY IS ALWAYS THE NUMBER ONE PRIORITY.
GRADING
The laboratory grade will count 25 % of the final Organic Chemistry lecture grade.
The laboratory grade is based on the experiments (each worth ten points), quizzes, and
notebook. The experiments are graded on the basis of the quality and quantity of the
product, and your technique. All experiments will count towards the final laboratory
grade; no experiments will be dropped. If you miss an experiment, speak with your
instructor as soon as possible, otherwise a grade of zero will be given for that experiment.
LABORATORY NOTEBOOK
Learning how to keep a proper lab notebook is part of your scientific training and you
will be expected to maintain a lab notebook for this Organic lab course. Part of your final
lab grade will be based on the adequacy of this notebook. A small bound composition
notebook (9 3/4 X 7 1/2 inches) is required. It will be graded during the semester and/or
collected at the end of the semester. It should be kept up to date at all times. Folders or
spiral notebooks are not acceptable. The notebook must include the following
information on numbered pages, unless specified differently by your instructor:
1) Start each new experiment on a new page.
2) Write the title of the experiment and the date it is preformed.
3) Write the balanced equation.
4) List the reactants, including the number of grams and moles of each. A reactant is any
reagent to the left of the arrow in the balanced equation.
5) Calculate the theoretical yield, showing all calculations.
6) Briefly outline the procedure.
7) Copy the class notes, including precautions and changes.
8) Record your results, including your actual yield and percent yield.
Steps one through six should be done before coming to class. Step seven
is written at the start of class and step eight is entered into your notebook
at the end of the experiment.
USING THE BALANCES

1) Start with the balance reading 0.00, press tare if it is not reading 0.00. The letter "g"
(grams) should always appear on the upper left hand of the display.
2) Place a large piece of paper and a beaker on the balance (always weigh solids in a
beaker, the paper is there in case you spill a chemical, it will be caught by the paper and
not corrode the pan of the balance).
3) Press tare so that balance again is reading 0.00.
4) Add the solid to be weighed out into beaker until desired weight is displayed.
5) Stop and clean up any spills immediately.
6) Never return excess chemicals to the container, pass them on to the next person or
dispose of them properly. Put tops on the containers immediately after use. The tops are
not used for anything else, don't put chemicals in them.
7) Remove the beaker, press tare to return balance to 0.00.
HEATING IN THE LAB

You will be required to use flask heaters, or a Bunsen burner flame as a heat
source throughout the two semesters of Organic Chemistry Lab. Read the procedures and
precautions for each experiment, to determine which heat source is necessary for that
experiment. If a Bunsen burner flame is to be used, make sure that no flammable
material, such as, solvents is in your hood. Also, make sure clothing (for example, shirts,
sweaters, and ties) and long hair, especially if you lean over, are kept away from the
flame. Never heat anything in a completely closed system.
BUNSEN BURNERS
1) Attach a hose from the Bunsen burner to the gas outlet (indicated by a blue color)
2) Adjust the bottom valve of the Bunsen burner so that it is open slightly.
3) Turn the gas on.
4) Using the gas lighter, light the Bunsen burner. If the burner will not light, open the
bottom valve of the burner or the gas outlet valve a little more.
5) After the burner is lit, turn the bottom valve to adjust the height of the flame and rotate
the barrel of the burner to adjust the flame size and intensity.
6) Always turn the Bunsen burner off by using the gas outlet. Always use a wire gauze
when using a flame as a heat source.
FLASK HEATERS
Never plug the Flask Heaters directly into an outlet, always use a Heat Control, which is
plugged into an outlet. Usually a setting of 15 is sufficient to heat most reaction mixtures
to boiling. Do not get the flask heater wet.
DISTILLATION TECHNIQUE
1) Always use a boiling chip, never add a boiling chip to a hot liquid.
2) Distill slowly, 1-2 drops per second.
3) The distillation receiver is always a round bottom flask.
4) All glass joints must fit tightly together, use rubber bands.
5) The tip of the temperature probe should be positioned properly (see page 95).
6) When collecting an organic product, the entire distillation apparatus must be dry.
7) Cooling water for the condenser, enters at the lower end of the condenser and exits at
the top. Use a reasonable, low pressure rate of water flow.
8) Distillation products to be submitted for grading must be dry (not cloudy). If the
product is cloudy, dry it with a drying agent and then decant the product into a dry bottle
before handing it in to the instructor.
9) Never leave a distillation unattended.
REFLUX TECHNIQUE
Reflux (see Figure 2, p. 95) is a method used to heat a reaction mixture to its boiling
point without losing any of this mixture through evaporation. The heat
provides the energy necessary for product formation. A good rate of reflux is
a mixture that is gently boiling, with vapor condensing no faster than 1
drop/second from the condenser. Follow the same rules as if distilling.
(boiling chips, grease, etc.) Vapors should never reach more than one quarter
of the way up the condenser. If vapors go higher in the condenser or come out
the top of the condenser, remove the heat source immediately.
RECRYSTALLIZATION TECHNIQUE
1) Steps one and two (see Figure 1, p. 94) should be set up before starting the
recrystallization process.
2) In a beaker add two boiling chips, the solid to be recrystallized, and the minimum
amount of solvent or in the amount directed. The minimum amount of solvent is the
amount of solvent that will dissolve the solid at the boiling point of the solvent, plus
approximately 10%.
3) If directed, let the liquid cool for two minutes and add a spatula full of charcoal, then
heat the mixture back to boiling. The charcoal is used to remove impurities.
4) Filter the mixture through a pre-heated powder funnel to remove any undissolved
impurities and the charcoal. The mixture that is being filtered must remain at or just
below its boiling point during the entire filtration. If solid starts to recrystallize in the
powder funnel, notify the instructor. Use a "Hot Hand" to grab the hot beaker.
5) Cool the collected liquid in an ice/water bath (use approximately 50% ice and 50%
water) until the entire contents of the beaker is ice cold (feel the outside of the beaker).
Occasionally stir the cooling solution.
6) Vacuum filter the cold mixture, rinsing the beaker with the filtrate if necessary, and
save the purified solid.
FILTERING AND DRYING SOLID:

1) Make sure the filtration apparatus is set-up as shown on p. 94, Figure 1, step 4.
2) Turn on the vacuum and mat down the filter paper with the solvent you are using
before starting to filter.
3) When beginning to filter, make sure that there is a proper seal between the funnel and
the filter flask by pushing down on the funnel.
4) When all of the liquid has filtered into the filter flask, it is usually a good idea to press
down the solid in the funnel with a clean cork or large spatula.
5) When finished filtering then close the vacuum.
6) Remove the solid from the filter paper and store it in a large beaker.
FILTER AID
This is a solid that sits on the filter paper and acts as a barrier to protect the filter paper
from the solid to be filtered out. It is used because the compound to be filtered consists
of very small particles that would clog up or go through the filter paper.
DRYING ORGANIC LIQUIDS (THE REMOVAL OF WATER)

A drying agent (ex. sodium sulfate) is a solid that removes water from an organic
liquid. The organic liquid is dry if it is clear and some of the drying agent swirls freely.
Start by adding a small spatula full of the drying agent to the liquid to be dried. If the
liquid is cloudy or all of the drying agent clumps together or sticks to the Erlenmeyer
flask, then there is still water present and more drying agent is needed. Add another
spatula full. The drying of an organic liquid should always be done in a stoppered
Erlenmeyer flask, not in a beaker. Always put the top back on the drying agent bottle
immediately after use.
DRYING GLASSWARE
1) Use the plastic squeeze bottle with acetone located at the front desk.
2) Squeeze acetone through the equipment needed to be dried and collect it in a beaker
(place this used acetone in the recycling container). This washes out the water.
3) Using an air jet (indicated by an orange color), gently blow air through the piece of
equipment so that the acetone evaporates. It should only take 10-15 seconds to evaporate
the acetone.
USES OF THE SEPARATORY FUNNEL:

1) To mix reagents.
2) To separate a liquid from another insoluble liquid.
3) To add a reagent dropwise to a reaction mixture.
Always remove the hollow stopper before dispensing any liquid from the separatory
funnel. In addition, drain the bottom layer and pour the top layer from the funnel.
THEORETICAL YIELD
The theoretical yield (TY) of a reaction is calculated before the start
of the experiment so that the student can know how much product to expect if
100 % of the reactants react to give the desired product. The calculation of
the theoretical yield can be performed in the following three steps:
1) Balance the equation.
2) Calculate the number of moles for each reactant using the following formula:
moles = grams / molecular weight
3) Calculate the TY based on each reactant using the following equation:
TY = (moles of reactant) (MW of product) {(moles of product)/(moles of reactant)}
The last term in this equation, the ratio {(moles of product)/(moles of reactant)} is
obtained from the coefficients of the balanced equation.
EXAMPLE
What is the theoretical yield of ethyl iodide given the following information:
6CH3CH2OH + 2P + 3I2
6CH3CH2
Ethanol
I + H3PO3
Ethyl iodide
The procedure calls for the addition of 7.9g of ethanol, 1.4g of phosphorus, and 10g of
iodine.
STEP 1: The equation is already balanced.
STEP 2: Calculate the number of moles for each reactant. Only compounds to the left of
the reaction arrow are reactants. Calculating the number of moles of ethanol,
phosphorus, and iodine:
Moles of ethanol = 7.90 / 46.07 = 0.171 moles
Moles of phosphorus = 1.40 / 30.97 = 0.0452 moles
Moles of iodine = 10.00 / 253.81 = 0.03940 moles
10
STEP 3: Calculation of the TY based on ethanol:

TY = (0.171) (155.97) (6/6) = 26.6g of ethyl iodide
Calculation of the TY based on phosphorus:
Calculation of the TY based on iodine:
The correct TY is the lowest number of grams calculated in step 3, therefore, the limiting
reagent for this reaction is iodine and the correct TY for ethyl iodide is: 12.29g
PERCENTAGE YIELD
The percentage yield (%Y) is calculated at the end of the experiment to
show the student how well he or she performed the experiment and about the
limitations of the experiment imposed by the nature of the reaction.
Calculate the percentage yield using the following equation:
%Y = (Actual Yield)/(Theoretical Yield) x 100
HANDING IN PRODUCTS
Unless otherwise instructed, the product prepared is given to the instructor in a labeled
bottle or envelope. On the label is neatly printed the student's name, the name of the
product, the actual yield, and the percent yield.
11
MELTING POINT
INTRODUCTION
The melting point and the freezing point can be defined as the temperature at which a
liquid and a solid phase of a compound exist in equilibrium at a pressure of one
atmosphere. The purpose of this experiment is to gain experience in the use of the meltemp apparatus and to learn what useful information melting points can tell us. Organic
chemist use this physical constant for two important reasons. Because it is highly
unlikely that two substances would have the exact same melting point, the possible
identity of an unknown pure solid can be determined by simply taking its melting point.
The second reason why chemists use melting points is to determine if a substance is pure
or impure. A pure substance will have a sharp narrow range (2-3C) melting point,
while an impure substance will have a lower, wider range melting point.
Throughout both semesters of organic chemistry lab, students will be synthesizing
different solid compounds. One method to determine if the correct compound has been
synthesized and that the purity of this compound is acceptable is to take a melting point.
The student will be asked to take a melting point, before submitting certain products that
they make in future labs, therefore, learning the correct method to determine the melting
point now, will save you a lot of time and aggravation in the future.
A mixed melting point is a method used to positively identify an unknown solid.
This is done by mixing your unknown compound with a known compound that you think
could be your unknown. If the unknown and the known that you mixed with it are the
same compound, then you will get a sharp melting point range, identical to the melting
point of the unknown taken by itself. However, if you mixed your unknown with a
known compound that is different from your unknown, you introduced an impurity into
your unknown and the melting point will be lower and have a wide range. A good
example of this last fact is that salt (the impurity) is placed on icy roadways (the ice is
assumed to be pure and will melt at 0) to melt the ice because the ice will now melt at a
lower temperature.
PRECAUTION - parts of the DigiMelt apparatus are hot and will easily burn you.
12
HOW TO TAKE A MELTING POINT

1) Place a small amount of a sample into a capillary tube that is open only at one end.
Either by gently tapping the capillary tube on the bench top or by gently vibrating the
tube with a file, allow the sample to travel to the closed end of the tube. There should be
approximately 5 mm. of sample in the capillary tube, just enough to see it clearly.
2) Turn the switch on the DigiMelt apparatus to the "on" position.
3) The START temperature should read at least 30 below the melting point of the
sample.
4) The STOP temperature should be 10C above the melting point.
5) The rate of heating called the RAMP rate should be 2C / minute.
6) Record the melting point range of your sample. The low end of this temperature range
is when the sample first starts to melt and the high end is when all of the sample has
melted.
PROCEDURE
1) Before class, record the literature melting points for all the compounds listed on the
back of the Melting Point Data Sheet. Record the source of this information.
2) Take the melting point of any three known compounds that are found under the hood.
Record all of your results in your notebook and then on the Melting Point Data Sheet.
3) Take the melting point of the unknown that was given to you. Set the START at
80C, the STOP at 170C RAMP rate at 10C / minute.
4) Take a second, more accurate melting point of your unknown by setting, the START
temperature should read at least 30 below the melting point of the sample the STOP
temperature should be 10C above the melting point the rate of heating called the RAMP
rate should be 2/ minute. Repeat this step with a new sample of your unknown to verify
your results.
5) Take a mixed melting point by placing a small amount of unknown on your watch
glass and adding about 1/5 as much of a known compound. This known compound
should hav
5). Mix them well and take its melting point. Do as many mixed melting points as
needed to identify your unknown, but at least two mixed melting points should be done.
6) Write your results in your notebook and then on the data sheet which will be
submitted to your instructor.
13
NAME_________________________
Pre-lab
LITERATURE MELTING POINTS OF SOME
ORGANIC COMPOUNDS
COMPOUND
LITERATURE MELTING POINT, C
Acetanilide
__________
Fluorene
__________
Benzoic Acid
__________
Benzamide
__________
Urea
__________
Glucose Pentaacetate
__________
Phenacetin
__________
Benzoin
__________
o-Chlorobenzoic Acid
__________
Anthranilic Acid
__________
Benzilic Acid
__________
Adipic Acid
__________
Salicylic Acid
__________
Benzanilide
__________
Source________________________________________________________
14
NAME_________________________
DATE ________________
LOCKER NUMBER _______
LAB DAY AND TIME ______________
MELTING POINT DATA SHEET

Results of Three Known Compounds listed in the Table on the Back
Known Compound
Literature M .P.
Observed M .P. Range
Results of Unknown
Unknown M.P. Range (taken quickly) _______________
Unknown M.P. Range (taken slowly) 1)_______________
2)_______________
Results of Mixed Melting Points

Compound Mixed with Unknown
Observed M.P. Range
UNKNOWN NUMBER __________

NAME OF UNKNOWN ____________________________
GRADES: Pre-Lab (20):_____ Experimental Technique (30):_____

Yield & Purity (30):_____ Post Lab Questions (10):_____ Lab Report Grade = _____
15
RECRYSTALLIZATION
INTRODUCTION
The purpose of this lab is to learn the technique of recrystallization and how to choose
a recrystallization solvent. Recrystallization is a process used to purify solid
compounds. In addition you will identify your unknown based on melting point.
In future experiments, you will be synthesizing different solid compounds. To assure
yourself and your lab instructor that these compounds are pure, you will be required to
perform a recrystallization at the end of each lab, before handing in your product for
grading. Therefore, it is important that you understand this technique and have this
procedure written down in your notebook so that you can refer back to it when necessary.
Before we look at recrystallization in detail, it is necessary to define the term
solubility. Solubility is the extent to which a substance (called a solute) mixes with a
liquid (called a solvent) to produce a homogeneous system (called a solution). The
importance of solubility can be seen in every experiment preformed in this class and in
many aspects of every day life. Reactants, used in future experiments, will be dissolved
in a suitable solvent. This lowers the activation energy so that the reaction can proceed to
products more easily. Solubility also plays an important roll in both chromatography
experiments. Pharmacy students, in future courses, will learn that drugs taken orally need
to be water soluble and fat-soluble at the same time for optimal adsorption in the blood.
The first part of today's experiment deals with the solubility of a pure solid compound
in a wide range of polar and nonpolar solvents (the compounds in the chart of the Data
Sheet are in increasing polarity order). The degree of solubility is important to determine
a good recrystallization solvent for this solid if it needs to be purified. The definition of a
good Recrystallization Solvent is:
1) A solvent that will dissolve a large amount of the solute (the compound to be purified)
when the solvent is hot and only a very small amount of solute when the solvent is cold.
2) Impurities will not dissolve in hot or cold solvent.
3) Ideally the solvent should also be cheap, nontoxic, and nonflammable.
In the second part of this experiment you will recrystallize an impure solid compound
using the best recrystallization solvent. The two unknowns are either benzoic acid or
acetanilide. The recrystallization process can be summed up as follows. The solid to be
purified is dissolved in a minimum amount of boiling solvent. The boiling mixture is
filtered to remove all insoluble impurities. The filtrate (the liquid that was collected after
the filtering) is cooled to precipitate the solid. The solvent is filtered off, leaving the
purified solid. One can see that recrystallization works because most compounds are
more soluble in hot solvent than in cold solvent. Finally the melting point can be used to
determine if your unknown is benzoic acid or acetanilide.
16
PROCEDURE
To prepare for this experiment properly, read how to use the balances (page 5),
filtering and drying solids (page 8) and the recrystallization technique (pages 7 and 93).
PART 1: SOLUBILITY TEST FOR THE SOLID TO BE PURIFIED

KEY:
S = soluble (all solid dissolves in 3 mL of solvent)
I = insoluble (not all solid dissolves in 3 mL of solvent)
1) Before lab, record on the Solubility Data Sheet, the literature boiling points for the
solvents used in this experiment.
2) Add 0.1 grams of the solid to be purified in a test tube. Add 3 ml of solvent. Stir with
wood sticks and record if S or I. If S, then repeat step 1 using the next solvent. If I, then
proceed to step 3.
3) Heat the test tube with a beaker of very hot water, stir, realizing that if you heat the
test tube too long, some low boiling point solvents will evaporate. Record: S if all solid
dissolves or I if some solid does not dissolve.
4) Repeat steps 1 and 2 for every solvent that the instructor has (usually petroleum ether,
acetone, ethyl acetate, ethanol, and water are the solvents tested) directed you to test.
5) All results should be recorded in your notebook and then on the solubility data sheet.
PRECAUTION: All of the solvents used in Part 1, except water, are flammable. Do
not start Part 2 until you are directed to do so by the instructor.
PART 2: RECRYSTALLIZATION OF AN IMPURE SOLID

(see Figure 1, page 94)
1) Place 1.0 gram of impure solid into a 250 mL beaker. Add 20 mL of the
recrystallization solvent and 2 boiling chips to the beaker. Do not take the pure solid that
was used for the solubility tests.
2) Set-up steps one and two of the apparatus as shown in Figure 1, page 94.
3) Heat the contents of the beaker to boiling with either a flask heater or Bunsen burner
as advised by your instructor; observe the sample! If your sample hasn't completely
dissolved after the mixture has been boiling for a couple of minutes,
add an additional 10 mL of solvent; reheat to boiling temperature and observe again.
17
It may be necessary to add more solvent to dissolve the crystals ( add in 10 mL

increments). As the beaker is being heated, heat the powder funnel and filter paper with
gentle steam.
4) As soon as the crystals have been dissolved in the hot solvent, add a small amount of
charcoal using a micro spatula, continue to heat for 1 minute, then shut off the heating
source.
5) Without letting the contents of the beaker cool down, pour the mixture in the beaker
through the preheated powder funnel that contains the filter paper. Use the "Hot Hand"
to grab the hot beaker. If crystals are formed during filtration, reheat to a boil then allow
the solution to cool by itself very slowly. After the beaker that contains the filtrate has
cooled to close to room temperature and crystals have formed, cool this beaker an
ice/water bath until it is as cold as the ice water.
7) Filter the purified solid through your Buchner funnel. This is done by wetting the
filter paper in the Buchner funnel with the solvent used to crystallize. Turn the vacuum
(yellow handle) on. When you are sure that the filter paper is matted down, pour the
solid mixture in your beaker, into the Buchner funnel. The solvent should drain into the
filter flask and the solid should be caught on the filter paper in the funnel. You should
see no solid in the filter flask. If you can't get all of crystals out of the beaker, pour some
or all of the filtrate (the solvent that drained into the filter flask) back into the beaker, stir,
and filter again.
8) Store your purified solid in a clean, dry 50 mL beaker in your locker until the
following lab period.
9) Please note this procedure should be applied whenever you recrystallize a solid.
10) Next lab period, you will take a melting point of your dried solid to check its purity.
Identify your unknown based on melting point. You will also measure the weight of the
purified solid and hand it in using a sample vial or envelope. Put a label on the vial with
the following information:
Your Name
Product Name
M.P. Range = _______C
% Recovered =_________
The % Recovered is calculated as follows:
% Recovered = (final weight/starting weight) X 100
18
NAME_________________________
DATE ________________
SOLUBILITY DATA SHEET

CHART OF SOLUBILITIES TO DETERMINE THE BEST
RECRYSTALLIZATION SOLVENT FOR ____________________
KEY:
S = very soluble (all solid dissolves in 3 mL of solvent)
I = insoluble (not all solid is soluble in 3 mL of solvent)
Solvent
Petroleum
Ether
Boiling Point
Cold
Hot
Good Recrystal. Solvent (yes/no)
Acetone
Ethyl Acetate
Ethanol
Water
Which of the solvents listed above is the best recrystallization solvent for the solid
you tested? Why?
Weight of Crude Solid ______________g

Weight of Recrystallized Solid ____________g
Melting Point Range _________________C
Percent Recovered ______________%
Name of unknown__________________

19
DISTILLATION
INTRODUCTION
Distillation is a process used to purify a liquid. The purpose of todays experiment is for
the student to become familiar with how to set-up the apparatus used in a distillation and
to compare two different types of distillations. These two different types are called
simple distillation and distillation with an unpacked column.
The reason why distillation works can easily be expressed by looking at Raoult's Law,
which states that the vapor above a boiling solution will always contain more of the lower
boiling point component than the solution that is boiling. In today's experiment we will
start with a 50/50 solution of acetone (B.P.= 56C) and water (B.P.= 100C). As the
solution is heated and starts to boil, the vapor above the boiling solution will contain
more acetone, the lower boiling point liquid. As this acetone rich vapor moves away
from the heat source and cools, this new solution still contains more acetone and less
water. Eventually, this acetone rich solution will be vaporized again. This vapor will
contain even more acetone and less water. Depending upon the amount of surface area
between the boiling liquid and the water cooled condenser, many of these vaporizations /
condensations can take place. Therefore, the more surface area, the greater the separation
of the two liquids.
In today's experiment, the student will distill a solution of acetone (some students will
be familiar with acetone as it is the solvent used to remove nail polish) and water, trying
to separate, as best as possible, the two liquids. This will be accomplished by collecting
three fractions and measuring their volumes. Fraction I will be collected from a
temperature range of 56 to 62, therefore, this fraction contains only acetone. Fraction II
will be collected between 63 to 90. This second fraction contains a mixture of acetone
and water. The last fraction, fraction III, is the residue. This fraction contains only water.
Ideally, to achieve the best separation, one should get all the acetone in fraction I, no
fraction II, and all the water in fraction III.
WHEN DISTILLING, ALWAYS:
1) Add two boiling chips to the distilling flask. Never add a boiling chip to a hot liquid.
2) Use a thin film of grease whenever glass touches glass. All glass joints must fit tightly
together, use rubber bands.
3) Insert thermometer probe into the adapter. The tip of the probe should be just below
the junction in the three way connecting tube.
4) Cooling water for the condenser enters at the lower position and exits at the top, turn it
on slowly.
5) A good rate of distillation is 1 drop/second.
6) The distillation receiver is always a round bottom flask.
7) Never leave your distillation unattended.
20
PRECAUTION
Acetone is flammable, it should not be left in an open container on the bench top. The
joints of the distillation set-up must be tightly fitted together.
PROCEDURE
1) Add 15 mL acetone, 15 mL of water, and 2 boiling chips to a 100 mL round bottom
flask (RBF).
2) Set-up the apparatus as shown for a simple distillation (Figure 3, page 96). Make sure
all glass joints are tight.
3) Turn on the water very slowly, until you see a slow, but steady stream of water
coming out of the condenser.
4) Get your apparatus checked by your instructor.
5) Heat the solution with a flask heater and heat controller so that the rate of distillation
is one drop per second.
6) At a temperature of just above 62C, turn off the heat controller and change the
receiving flask from a 50 mL to a 25 mL RBF. Make sure you did not loosen any glass
joints and then start to heat again.
7) At 90C, turn off the heat controller. Let the residue in the 100 mL RBF cool.
8) Measure and record the three volumes that were collected. Dispose of the fractions as
directed.
9) Repeat this procedure, but set-up an unpacked column distillation apparatus in step 2
(Figure 4, page 97). It is not necessary to clean or dry any equipment.
10) Obtain an unknown acetone/water solution from your instructor and measure the
volume (do not add any additional water). Determine the amount of acetone present in
your unknown solution by using distillation through an unpacked column, as in step 9.
11) Record your results in your notebook and then on the data sheet.
21
NAME_________________________
DATE ________________
DISTILLATION DATA SHEET

SIMPLE DISTILLATION (NO COLUMN)
VOLUMES COLLECTED
T = 56 to 62C _________mL
T = 62 to 90C _________mL
T = 90 to 100C ________mL
UNPACKED COLUMN
VOLUMES COLLECTED
T = 56 to 62C _________mL
T = 62 to 90C _________mL
T = 90 to 100C ________mL
UNKNOWN SOLUTION DISTILLATION

Starting Volume __________mL
Volume Collected between 56 to 62C___________mL
Percent acetone in unknown solution ______________%
Which method of distillation (no column or unpacked column) was the best? Why?
GRADES
Pre-Lab (20):_____ Experimental Technique (30):_____
22
RESOLUTION OF RACEMIC PHENYLSUCCINIC ACID
INTRODUCTION
Because enantiomers have mostly identical chemical and physical properties, their
separation (called a resolution) requires special techniques. Resolution via
diastereeomeric salt formation, first accomplished in 1853 by the father of
stereochemistry, Louis Pasteur, will be the method of resolution demonstrated in this
experiment. Racemic phenylsuccinic acid (RS-PSA) will be resolved using the optically
pure base, S-(-)-Proline (S-Pro)* or R(+)-Proline (R-Pro).. The optical purity of some
samples can be determined using a technique called polarimetry. We will not be telling
you whether you are using S-Pro or R-Pro ! - you will use polarimetry of the PSA sample
that you isolate to discover the stereochemistry of the Proline that you used.
When an acid is mixed with a base, a salt results and this is the case when RS-PSA is
mixed with S-Pro, using isopropanol as a solvent. Two different salts form. The first salt
consists of (S-PSA)-(S-Pro)2, that is, for every one molecule of S-PSA, there are two
molecules of S-Proline associated with it. The second salt is composed of (R-PSA)-(SPro). These two salts can now be separated because of their solubility difference in
isopropanol. The (S-PSA)-(S-Pro)2 salt, being less soluble in the isopropanol,
precipitates out of solution and can be isolated by filtration. The more soluble (R-PSA)(S-Pro) salt remains dissolved in the filtrate. The S-PSA can be liberated from its proline
salt form by the addition of hydrochloric acid. The converse happens with RS-PSA and
R-Pro (see diagram above!).
The resolution of enantiomers is a very important topic, especially when dealing with
chiral drugs. For example, with Ibuprofen (Motrin, Advil), the S-enantiomer has all of
the anti-inflammatory activity, while the R-enantiomer has no effect. With
Chlorpheniramine (Chlortrimeton), the S-enantiomer contains all of the antihistamine
activity, while the R-enantiomer has a sedative side effect.
*Stephani, R. and Cesare, V. J. Chem. Educ., 1997, 74, 1226.

** S-(-)-Proline is also called L-(-)-Proline , R-(+)-Proline is also called D-(+)-Proline
23
PROCEDURE (Review the reflux technique (p. 7) and set-up (Figure 2, p. 95),
(All equipment should be dry through step 5)
1) Weigh out 1.94g of racemic phenylsuccinic acid in a 150 mL beaker and dissolve it in
50 mL of 2-propanol. Transfer this solution to a clean and dry 100 mL RBF using your
long stem funnel.
2) Add 1.15g of unknown proline (break up any clumps) to the 100 mL round bottom
flask (RBF) using your powder funnel. Use 10 mL of 2-propanol to rinse the small
amount of proline that remains in the beaker. Swirl the flask for several minutes. All of
the proline will not dissolve. Obtain a stir bar from the instructor.
3) Reflux (Figure 2, p. 95) and stir with magnetic stir bar (and stir plate) and with a flask
heater and heat controller for 20 minutes.
4) Air cool the flask to room temperature. This takes about 10 to 15 minutes.
Occasionally swirl the mixture during this time. A lot of solid should be seen when the
flask reaches room temperature. Remove the magnetic stir bar with a magnetic stir
and return the stir bar to the instructor.
5) Stir the mixture in the flask for one minute and then vacuum filter the mixture through
clean, dry equipment. The filter paper should be matted down with 2-propanol. Use the
filtrate to remove all of solid from the flask. Discard the filtrate as directed by the
instructor. Wash the solid with 2 x 15 mL of acetone. Leave the vacuum on for 2 minutes
after the second acetone wash and then press down the solid with a hollow stopper to
remove as much liquid as possible. Dry the solid between two pieces of filter paper.
Discard the acetone filtrate as directed by your instructor.
6) Add 10 mL of 6M HCl to a 100 mL beaker and clamp it in an ice/water bath. When
this solution is cold, add all of the solid from step 5. Stir for about 5 minutes.
7) Vacuum filter the mixture (clean the filtration apparatus with water and mat down the
filter paper with water, the equipment does not have to be dry). Wash the solid in the
Buchner funnel with 2 x 15 mL of water. Let the solid dry in a large beaker until the next
lab period. Discard the filtrate as directed by your instructor.
8) After recording the weight, use a polarimeter to measure the optical rotation, a, of your
phenylsuccinic acid. Do this by adding all of your PSA to a 10 mL graduated cylinder,
add 7 to 8 mL of acetone and stir to dissolve all of the solid. Then add more acetone until
the solution is exactly to the 10 mL mark of the cylinder, stir again. Add this solution to
the polorimeter cell until it is full. Place the cell into the polarimeter record the observed
Be sure to determine whether the optical rotation is plus + or minus-.
Calculate the specific rotation [] and the percent optical purity (% OP) using the
formulas shown on the data sheet. Determine if you have resolved R-Phenyl succinic
acid or S-Phenyl succinic acid.
24
NAME________________________________ LOCKER #______________

DATE________________
LAB DAY AND TIME_________________
RESOLUTION OF PHENYLSUCCINIC ACID

DATA SHEET
OVERALL RESOLUTION EQUATION:
DATA FOR PHENYLSUCCINIC ACID

[]max = + _173.3_ (c = 1, acetone) (from CRC Handbook of Chemistry and Physics)
Theoretical Yield = ________g
RESULTS
Weight of (+)-PSA Recovered =_________g
Percent Yield = __________
Observed Rotation = ___________ Record if it is plus + or minus-.
[] = ____________ (c = _________, acetone)
% Optical Purity = _________
My resolved Phenylsuccinic acid is R or S.CIRCLE THE CORRECT ISOMER.
[] = / (lc)
where
l = length of the cell in decimeters (10 cm = 1 dm)

c = concentration in g/mL
% OP = ([]/[ ]max) x 100
where []max = [] of optically pure PSA in acetone

25
SYNTHESIS OF TERTIARY BUTYL CHLORIDE

CH3
CH3
C OH
CH3
HCl
CH3
CH3
tert-Butyl Alcohol
C Cl
H2O
CH3
Hydrochloric
Acid
tert-Butyl Chloride
INTRODUCTION
In this experiment, the student will see that tertiary alcohols react almost
instantaneously with hydrohalic acids at room temperature to form an upper layer of an
alkyl halide. The student will also become familiar with some of the uses of the
separatory funnel and also how to dry organic liquids using drying agents. Before
coming to lab, read the uses of the separatory funnel (page 8) and drying organic liquids
(page 8).
PRECAUTIONS
1) Concentrated hydrochloric acid can cause severe burns.
2) Tertiary butyl chloride is very flammable, therefore, no flames are to be used today.
3) Always vent the separatory funnel when mixing compounds and remove the hollow
stopper when dispensing liquids from it.
PROCEDURE
1) To your separatory funnel add 7.86 g (10 mL) of tert-butyl alcohol and 25 mL of
concentrated hydrochloric acid. (Concentrated hydrochloric acid has a molarity of
12.4M. Knowing this value and that M = mol/L, the number of moles can easily be
calculated. Knowing that the MW of HCl is 36.46g/mol., the number of grams of HCl
also be calculated.
* J.F. Norris, et al, Org. Syn., 1928, 8, 50.
26
2) Gently swirl the contents of the separatory funnel for one minute, then stopper it with
your hollow stopper. Invert and vent the separatory funnel by opening the stopcock to
release the pressure. Make sure you hold the hollow stopper in place when you invert the
funnel. Repeat the shaking, inverting, and releasing of pressure, slowly at first. As the
pressure decreases, gradually increase the shaking. This is done for approximately five
minutes.
3) Clamp the stoppered funnel to a ring stand and let it stand until both layers are clear.
This will take at least 20 minutes. During this time, the student should set up the
distillation apparatus used later in this experiment.
4) When both layers are clear, drain off and discard the lower layer.
5) Add 10 mL of saturated sodium bicarbonate solution to the top layer in the separatory
funnel. Gently swirl the unstoppered funnel for two minutes, and then stopper it, invert,
and release the pressure. This is again repeated, gradually increasing the shaking. Be
sure to frequently vent the funnel.
6) After letting the layers separate for one minute, drain off the lower bicarbonate layer
and discard it.
7) Add 10 mL of water to the top layer, stopper, invert, and vent several times as done
previously.
8) Let the layers separate for one minute and then drain off and discard the lower water
layer.
9) Transfer the top tert-butyl chloride layer to an Erlenmeyer flask and dry it with
sodium sulfate (see page 8).
10) Using your long stem funnel with a very small piece of glass wool, decant the t-butyl
chloride from the sodium sulfate into your 50 mL round bottom flask (RBF).
11) Distill tert-butyl chloride using a simple distillation set-up (Figure 3, page 96) with a
flask heater and heat controller. Collect the product up to and including 52C or until the
distillation stops. Use a 25 mL RBF cooled with ice water as the receiving flask.
12) Pure tert-butyl chloride is a clear, colorless, liquid. If your product is cloudy, dry it
with sodium sulfate before handing it in.
27
ORGANIC CHEMISTRY PRE-LAB AND DATA REPORT

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
TITLE OF EXPERIMENT____________________________________________
BALANCED EQUATION:
Name of
Reactant
Grams MM
Product Coeffc.
b
Moles Reactant
Coeff.
Moles d
Produc
of
t
NAME OF PRODUCT____________________________________
Molar Mass ___________ M.P(solid)e or B.P.(liquid)e__________
RESULTS:
Actual Yield _________g
a.
b.
c.
d.
e.
Percent Yield _________%
Melting Point______oC
Use atomic weights rounded off to the nearest 0.1 atomic mass unit.
Moles = Grams/Molar Mass.
Coefficients from the balanced equation.
Moles of Prod.= (Product Coefficient/Reactant Coefficient) X Moles of Reactant.
From the Handbook of Chemistry and Physics, the Aldrich Catalog, or a website.
GRADING: Pre-Lab (20):_____ Experimental Technique (30):_____

28
SYNTHESIS OF 2-METHYL-2-BUTENE
CH3
CH3
CH2
C CH3
OH
CH3
H2SO4
CH3
H2O
CH C CH3
H2O
2-Methyl-2-Butene
2-Methyl-2-Butanol
(t-Amyl Alcohol)
INTRODUCTION
In this experiment, 2-methyl-2-butene, an alkene, will be synthesized, by the sulfuric
acid catalyzed dehydration of 2-methyl-2-butanol. This reaction demonstrates that the
more highly branched alkene will be the major product because the hydrogen nucleus on
the number 3 carbon is the easiest to remove. Can you name the minor product in this
reaction?
PRECAUTIONS
1) 2-methyl-2-butene and 2-methyl-2-butanol are flammable, therefore, no flames are to
be used today.
2) Be careful when using the sulfuric acid solution and the sodium hydroxide solution,
both will burn the skin.
3) The product, 2-methyl-2-butene, boils at a low temperature, therefore, it evaporates
very quickly. Do not leave it open to the air. You will notice that the receiving flasks
during the distillations are packed in ice/water. This is to keep the product from
evaporating.
* Whitmore, F.C., Rowland, C.S., Wrenn, S.N., Kilman, G.W., J. Am. Chem. Soc., 1942,
64, 2970.
29
PROCEDURE
1) Set up a simple distillation (Figure 3, page 96) with the following changes: use a 50
mL RBF that is packed in ice/water as a receiving flask and a 100 mL RBF as the
distilling flask. Use the large condenser and the hollow stopper in the set up. None of
this equipment has to be dry.
2) Add 20.0 mL of the sulfuric acid solution (34 %) to a 125 mL Erlenmeyer flask and
cool it in a beaker of ice water.
3) Slowly, with swirling and continued cooling of the flask, add 10.0 mL of 2-methyl-2butanol (tertiary amyl alcohol) to the 125 mL Erlenmeyer flask.
4) Using a long stem funnel, transfer the contents of the Erlenmeyer flask to the 100 mL
RBF of the distillation set-up.
5) Using a flask heater, distill until distillate is no longer obtained. This usually takes
between 10 to 20 minutes if the rate of distillation is one to two drops per second. There
will be liquid left in the 100 mL RBF. Remember that a good rate of distillation is 1 drop
per second!
6) Transfer the contents of the 50 mL RBF to a separatory funnel and add 5 mL of 10 %
NaOH solution. Swirl the unstopped funnel for one minute and then stopper it with your
hollow stopper and shake the funnel with frequent venting. Clamp the separatory funnel
to a ring stand and let the two layers separate. Drain off and discard the lower aqueous
layer as directed by your instructor.
7) Pour the top layer (2-methyl-2-butene) into a clean, dry 50 mL Erlenmeyer flask.
Cork and cool the flask in and ice/water bath and dry the product with sodium sulfate.
8) Decant the liquid through a clean, dry, long stem funnel that contains a small amount
of glass wool into a 50 mL RBF and distill using simple distillation (Figure 3, page 96)
with a flask heater and controller. All equipment must be clean and dry. Use the west
(thin) condenser and a 25 mL RBF that is packed in ice/water as a receiving flask.
Collect up to 43C as pure product.
9) Hand in the product today, as directed by your instructor.
30

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM
Product Coeffc. Moles d

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
CALCULATION OF THEORETICAL YIELD
Lowest moles of product ________ X MM of Product ___________=
RESULTS
ACTUAL YIELD ___________G PERCENT YIELD ___________%
a.
b.
c.
d.
e.
GRADING: Pre-Lab (20):______ Experimental Technique (30):_____

Yield & Purity (30):______ Post Lab Questions (10):_____ Lab Report Grade = ______
31
SYNTHESIS OF 2,4,4-TRIMETHYL-2-PENTENE AND ISOMER
CH3
4 CH3 C OH
H2SO4
CH3
CH3
4 CH3 C CH2
H2SO4
H2O
H2O
CH3
4 CH3 C CH2
Isobutylene
CH3
4 H2O
CH3
CH3 C CH2 C CH2
CH3
CH3
CH3 C CH C CH3
CH3
CH3
Overall equation:
CH3
4 CH3 C OH
H2SO4
CH3
tert-Butyl Alcohol
H2O
CH3
CH3
CH3
CH3 C CH2 C CH2
+ CH3
CH3
2,4,4-Trimethyl-1-Pentene
CH3
C CH C CH3
4 H2O
CH3
2,4,4-Trimethyl-2-Pentene
INTRODUCTION
When tert-butyl alcohol is heated in the presence of sulfuric acid, 2-methyl propene
(isobutylene) is produced. The mechanism for this reaction is similar to the synthesis of
2-methyl-2-butene, the last experiment.
Isobutylene has a boiling point of -7C, therefore, it is a gas at room temperature.
This isobutylene gas, if left in the presence of the sulfuric acid solution, will react further
and dimerize to give the following two isomers: 2,4,4-trimethyl-2-pentene and 2,4,4-trimethyl-1-pentene. If hydrogen gas and a catalyst, such as nickel, were allowed to react
with these two pentenes, 2,2,4-trimethylpentane would form. 2,2,4-trimethylpentane has
the common name iso-octane or synthetic gasoline. It has been assigned an octane
number of 100. Compare this rating, to the octane number of the gasoline that you use in
your car. Most unleaded gasoline has an octane rating between 87 and 92.
When calculating the TY for this experiment, since both pentene products are
collected together, add the theoretical yield of both pentene products to get the correct
overall TY. This is done because both of the pentenes boil within 5C of each other and
would be difficult to separate using simple or column distillation.
* Whitmore, F.C., Ind. Eng. Chem., 1934, 26(1), 94-95.
32
PRECAUTIONS
1) Be careful with the sulfuric acid solution, it burns.
2) Both tert-butyl alcohol and the two pentene products are flammable. Use a flask
heater for the reflux and the distillation, do not leave them unattended. Make sure glass
joints are fitted tightly together.
PROCEDURE
1) Clamp a 100 mL RBF to a ring stand and add 28 mL of 50 % aqueous sulfuric acid
solution to it.
2) Slowly add 10.0 mL of tert-butyl alcohol and immediately attach a reflux condenser.
3) Using the flask heaters and controller, gently reflux (Figure 2, page 95) the solution
for 30 minutes. A good rate of reflux for this reaction is a gentle boil. During this time,
you can see the formation of an upper layer, which is the pentene products.
4) Cool the reaction mixture to room temperature by lowering the 100 mL RBF into an
ice/water bath. Leave the condenser on and the water running until the reaction mixture
is cool.
5) Add the reaction mixture to a separatory funnel and drain off and discard the lower
layer as directed by your instructor.
6) Add 20 mL of water to the top layer in the separatory funnel. Shake the funnel with
venting.
7) Drain off and discard the lower aqueous layer as directed by your instructor.
8) Add the top layer to an Erlenmeyer flask and dry it with a small spatula full of sodium
sulfate.
9) Decant the dried liquid through a long stem funnel that contains a small amount of
glass wool into a clean, dry 50 mL RBF.
10) Set-up a simple distillation (Figure 3, page 96) with a flask heater and controller, use
a 25 mL RBF as a receiving flask. The position of the temperature probe is important.
All equipment must be clean and dry. If you have some unreacted tert-butyl alcohol, it
will distill over at approximately 82C. Change the receiving flask at 90C if any alcohol
did distill over. Collect between 100 - 108C as pure product. The alkenes should be
clear and colorless, hand it in as directed by your instructor.
33

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

34
OXIDATION OF CYCLOHEXENE TO ADIPIC ACID

O
3
Cyclohexene
+ 8 KMnO4
+-
3 K O C ( CH2) C O- K+
4
Potassium
Permanganate
8 MnO2
+ 2H2O + 2 KOH
HCl
3 HOOC
CH2
CH2 CH2 CH2

Adipic Acid
COOH
INTRODUCTION
Double bonds can be cleaved by several oxidizing agents. The oxidizing agent to be
used in this experiment is potassium permanganate. The mechanism of this oxidation
involves the initial formation of a cis-glycol. The carbon-carbon bond of the glycol is
then further oxidized by the permanganate and is cleaved to yield the dicarboxylic acid,
adipic acid. Adipic acid is used in the manufacturing of nylon.
PRECAUTIONS
1) Be careful with the potassium permanganate, it stains clothes and skin.
2) Be careful with the concentrated hydrochloric acid, is severely burns.
PROCEDURE
1) In a 100 mL RBF, dissolve 4.13 g of potassium permanganate in 75 mL of hot tap
water (stir for 4 or 5 minutes with a magnetic stirrer).
2) Make a solution of 1.0 mL of cyclohexene in 5 mL of acetone. In approximately one
milliliter increments, add this solution into the 100 mL RBF (use a transfer pipet for the
addition). Gently stir the flask with the magnetic stirrer throughout the addition.
3) After the addition is complete, attach your large condenser to the RBF. With water
running up through the condenser, heat the flask very gently with flask heater for 20
minutes, continue the stirring. During this time, in a 400 mL beaker, dissolve 3 g of
sodium bisulfite in about 200 mL of hot water. Save this solution to clean all of your
equipment that will have a brown manganese dioxide stain throughout this experiment.
4) Allow the reaction mixture to air cool for 5 minutes.
* Golendeev, V.P., Trudy Gor'kovsk. Politekh. Inst., 1955, 11, 5-11.
35
5) Remove the condenser and add 2.0 g of sodium bisulfite in small increments over 10
minutes to the hot reaction mixture (use your powder funnel). Swirl and stir the mixture
for 4 or 5 minutes, then cool it in an ice bath to below room temperature.
6) While the flask is cooling, add 5 or 6 large spoonula's full of celite (see page 8, filter
aid) to 40 mL of water in a 100 mL beaker.
7) Using water, mat down a small piece of filter paper on the Buchner funnel of your
filtration equipment. With the vacuum on swirl and pour the celite/water mixture from
step six into the Buchner funnel. The 40 mL of water will filter through into the filter
flask and the celite should form a layer that completely covers the filter paper. Slowly
release the vacuum and discard the 40 mL of water from the filter flask.
8) Filter the cooled reaction mixture through the Buchner funnel that contains the celite.
Never fill the Buchner funnel much more than half way. The filtrate must be colorless.
9) Add 20 mL of water to the 100 mL RBF to rinse it. Pour this 20 mL of water onto the
brown solid (MnO2) in the Buchner funnel. Transfer the filtrate (the liquid in the filter
flask) to a 150 mL beaker (the beaker should be pre-marked for 15 mL) and give it to
your instructor until next lab period. Leave it uncovered.
NEXT LAB PERIOD (review recrystallization, pages 7 and 93)
10) Concentrate the filtrate to until 15 mL of liquid remains in the 150 mL beaker. Use
the Bunsen burner as a heat source.
11) As soon as you can, transfer the hot 15 mL of solution remaining in your 150 mL
beaker into a clean 100 mL beaker. Cool this solution in an ice/water bath until it is
below room temperature.
12) Acidify the 15 mL of solution in the 100 mL beaker until the pH = 1-2 by dropwise
adding concentrated hydrochloric acid. Stir the mixture after adding each drop of acid
and check the acidity using EMD pH strips. White crystals of adipic acid will precipitate
from the water. Cool this solution in an ice/water bath with occasional stirring until it is
below room temperature.
13) Vacuum filter the mixture and then combine your adipic acid with your lab hood
partner and recrystallize the adipic acid using about 5 to 10 mL of water as the
recrystallization solvent, did you look at pages 7 and 93?
14) Let the pure adipic acid dry in your locker in an open beaker until next period. Clean
and dry all glassware for next period.
36

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

37
SYNTHESIS OF 2-METHYL-4-HEPTANONE
INTRODUCTION
Many times starting materials are not readily available to synthesize the desired
product in one step. It is first necessary to synthesize, in one or more steps, compounds
that can then be converted into the final product. This experiment is an example of a
multi-step synthesis to obtain the desired product, 2-methyl-4-heptanone. Infrared
spectroscopy (IR) will be used to determine if the reactions were successful.
One of the most versatile synthetic reagents in organic chemistry is the alkyl or
aryl magnesium halide: the Grignard reagents. Grignard reagents were discovered by P.
A. Barbier and their chemistry was worked out extensively by his student, Victor
Grignard (Noble Prize, 1912).
In today's experiment, you will use one of two different "routes" to make the same
compound. Which Grignard and alkyl halide you use will depend on the Route you are
assigned! The First reaction involving the Grignard reagent is split into two steps:
In the first step, the Grignard reagent is prepared by reacting an alkyl halide, with
magnesium under anhydrous (no water) conditions (first equation). In the second step,
the Grignard reagent is allowed to react with an aldehyde to obtain the salt of 2-methyl-4heptanol. The salt is easily hydrolyzed by the addition water (second equation).
Finally, this alcohol will be converted to the corresponding ketone, 2-methyl-4heptanone, using sodium hypochlorite as the oxidizing agent (third equation).
* J. Chem. Educ., 1991, 68, 71.
38
PRECAUTIONS
1. Diethyl ether is extremely flammable; NO BUNSEN BURNERS are to be used
today.
2. All reactions are exothermic, add reagents cautiously and as directed.
3. Sodium hypochlorite is a bleaching agent, wear your lab coat.
4. When mixing in the separatory funnel, swirl gently with the stopper off. When
shaking, vent the separatory funnel frequently.
PROCEDURE
DO NOT CLEAN OR RINSE OUT ANY GLASSWARE UNTIL AFTER STEP #10
1) All apparatus must be cleaned and dried the lab period before starting this experiment.
2) Carefully insert the prepared calcium chloride tube into your thermometer adapter.
3) Set-up the apparatus as follows: clamp a 100-mL RBF to a ring stand and attach a
claisen connecting tube. To the side opening of the tube attach the large condenser. Place
the calcium chloride tube on top. To the opening of the claisen tube that is directly over
the flask, place a separatory funnel, which will function as an addition funnel. This setup remains the same until step #11.
4) Weigh out magnesium turnings (1.9 g) and grind them with a mortar and pestle for
approximately one minute, then transfer then to the 100 mL RBF. Add and a few crystals
of iodine. Carefully, place a magnetic stir bar into your 100 mL RBF.
5)Route A: Make a solution of 1-chloropropane (4.07 g, 4.54 mL) in 15 mL of diethyl
ether in the separatory funnel
Route B:Make a solution of 1-chloro-2-methylpropane (4.81 g, 5.45 mL) in 15 mL of
diethyl ether in the separatory funnel. Swirl the apparatus to make sure the halide/ether
solution is well mixed.
(Review precautions). Turn on the water to the condenser.
6) Begin adding, DROPWISE, a small amount of the 1-chloro-2-methylpropane/ether
solution to the flask (approx 40 drops). The contents of the flask should become cloudy,
small bubbles should appear, the ether should begin to boil and reflux and the iodine
brown color should disappear. Be patient, if after 5 minutes there is no sign of a reaction,
notify your instructor. Then begin stirring with magnetic stir bar. Make sure the flask is
centered relative to the stir plate.
7) Keeping the reaction under control, add the rest of the 1-chloroalkane/ether solution, a
portion at a time, to maintain a steady rate of reflux. (Approx. 1-2 drops/sec) After all
has been added, close the separatory funnel and heat the flask by using a beaker of hot
water so that the reaction mixture gently continues to reflux for 20 minutes.
39
8) Cool the reaction mixture in an ice/water bath to room temperature.

9) Route A: Make a solution of 3-methylbutanal (2.84g, 3.61 mL) in 15 mL of ether in
the separatory funnel
Route B: Make a solution of butanal (2.40g, 2.92 mL) in 15 mL of ether in the separatory
funnel
and then dropwise, add this solution to the 100 mL RBF with stirring. After the addition
is complete, reflux the reaction mixture with a beaker of hot water for 15 minutes. Cool
the reaction mixture to below room temperature before proceeding to the next step.
10) Carefully, with constant stirring, add 10 mL of water, in small portions, from the
separatory funnel to the reaction mixture. Stir for several minutes. IF you have time
AND the solution above the solids is clear, complete steps 11-14. If not, stopper the
flasks loosely, and continue at the next lab. Return the magnetic stir bar to the instructor.
PART 2
11) Decant the solution from the unreacted magnesium into a separatory funnel, it maybe
necessary to add 20-40 mL of additional ether to the reaction flask, add 10mL of water to
the separatory funnel, shake and vent, allow layer separation and discard the lower
aqueous layer in the waste container (NOT THE SINK).
12) Add 30 mL of 5 % sodium hydroxide (NaOH) solution, shake and vent, allow layer
separation, discard the aqueous bottom layer as above and transfer the top ether layer to a
100 mL RBF.
13) Distill the ether from a 100-mL RBF using hot water bath. (simple distillation; see
diagram on page 95 lab text, you can substitute a glass stopper for the thermometer) Your
product is the residue of the distillation; the ether, which distills over, is collected in the
"recovered ether" bottle. Cool the receiver with ice water.
14) Add 10 mL of acetic acid to the 100-mL flask that contains the 2-methyl-4-heptanol.
Clamp this flask in a small beaker of ice water for 2-3 minutes. With the flask still in the
ice water, carefully add 30-mL aqueous 2.1M sodium hypochlorite solution, in small
portions, gently stirring (with a magnetic stir bar) the mixture after each addition.
15) Remove the flask from the ice water and swirl the solution carefully while it returns
to room temperature. Return the magnetic stir bar to your instructor.
40
EXTRACTION TECHNIQUES USING DICHLOROMETHANE

Dichloromethane is denser than water and most organic compounds and will therefore
appear in the lower layer of the extraction. When you extract an aqueous layer 2 times,
you remove the lower layer after the first extraction, SAVE IT, and re-extract the
remaining upper aqueous layer with a fresh amount of dichloromethane. You will then
combine the two lower layers, which contain dichloromethane and whatever was
extracted into it. The upper layer is then disposed of properly.
16) Add 30 mL of water to the reaction in step #16 and transfer it to a separatory funnel.
Extract the aqueous solution 2 times with 30 mL of dichloromethane. Add 5 mL of water
to the combined dichloromethane extracts, shake and separate the lower organic layer.
17) Dry the dichloromethane layer with sodium sulfate, decant and distill off the
dichloromethane using a simple distillation. Cool the receiver with ice water bath. Distill
the light fractions (the low boiling point compounds) up to a thermometer temperature of
60O C, 20 degrees above the boiling point of dichloromethane. The 2-methyl-4-heptanone
remains as the residue of the distillation. Take an IR of this product. Label the key
peaks in the IR. Hand in the product as directed. Put the dichloromethane in the bottle
labeled "Recovered Dichloromethane".
41

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

42
SYNTHESIS OF ETHYL IODIDE

2P + 3I2
2PI3
Phosporus
triodide
6CH3CH2OH +
2PI3
6CH3CH2
I + H3PO3
6CH3CH2
I + H3PO3
Overall equation:
6CH3CH2OH + 2P + 3I2
Ethanol
Ethyl iodide
INTRODUCTION
This experiment demonstrates a second method that an alkyl halide can be
synthesized. Compare this method to the method used to synthesize t-butyl chloride. In
this experiment the student is actually performing two reactions. The first reaction is the
synthesis of phosphorus triodide. As soon has the phosphorus triodide is formed, it will
react with the ethyl alcohol to produce the alkyl halide, ethyl iodide. When the product
of a first reaction (phosphorus triodide) is used, without isolation or purification, as a
reactant in the formation of a second product (ethyl iodide), then these two reactions are
said to be done "In situ".
To calculate the theoretical yield of ethyl iodide, use the bottom, overall equation.
PRECAUTIONS
1) Phosphorus, Iodine, and Ethyl Iodide are dangerous. Avoid contact of these three
chemicals with the skin. Avoid breathing these chemicals.
2) Ethyl alcohol and ethyl iodide are flammable. During the reflux and both distillations,
all glass joint must be tightly fitted together.
* King, H.S., Org. Syn., 1933, 13, 60 - 65.
43
PROCEDURE 1) Clamp a 250 mL round bottom flask (RBF) to a ring stand and
add 1.4g of red phosphorus (0.045 moles) and 10 mL of absolute ethanol (0.17 moles)
using a powder funnel. Don't forget to add two boiling chip to the flask.
2) Slowly, a spatula-full at a time, add 10g (0.04 moles) of iodine through the powder
funnel and into the 250 mL RBF. Swirl the reaction mixture after each addition, gently
rocking the ring stand from side to side for 30 seconds. The RBF should get warm, due to
the exothermic reaction taking place. If the reaction mixture begins to boil, cool the flask
in 600 mL beaker of ice/water until the boiling stops, then re-start the addition of iodine.
3) After all of the iodine has been added, attach a reflux condenser (the "fat" condenser)
and swirl the mixture for several minutes.
4) Reflux (Figure 2, page 95) with a flask heater and controller for 30 minutes.
5) Cool the reaction mixture in ice/water, without removing the condenser, until the
contents of the flask are approximately at room temperature.
6) Distill the contents of the 250 mL flask. Set up a simple distillation (Figure 3, page
96). Use a flask heater and controller. Use a hollow stopper instead of a thermometer
adapter and thermometer. Use the same condenser that was used for the reflux, no need
to clean it. Use a 100 mL RBF as a receiving flask. Distill until there is no liquid left in
the 250 mL RBF. You will see a dark colored solid in the distilling flask and a yellow,
red or orange colored distillate in the 100 mL receiving flask.
7) Transfer the impure ethyl iodide from the 100 mL RBF to a separatory funnel and add
10 mL of 3% sodium hydroxide. Put the hollow stopper on the funnel. Invert and vent
the funnel several times. Shake the funnel more vigorously and continue to vent. Clamp
the funnel to a ring stand and allow the contents of it to separate into two layers.
8) Drain the lower layer (impure ethyl iodide) & save it. Discard the top aqueous layer.
9) Put the bottom layer back into the separatory funnel and add 10 mL of water. Shake
and vent the funnel several times, then let the two layers separate.
10) Drain the lower layer into an Erlenmeyer flask and dry it with sodium sulfate.
Discard the top, water layer.
11) Distill the dried ethyl iodide using a flask heater and a simple distillation (Figure 3,
page 96). Use a 50 mL RBF as a distilling flask and a 25 mL (RBF) as a receiving flask.
Use the west ("thin") condenser, the thermometer adapter, and the 150 degree
thermometer. All of the equipment must be clean and dry. Collect up to 73C as pure
product.
12) Ethyl iodide is a clear colorless liquid. Hand in the product in a 30 mL sample bottle
with the usual label.
44

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

45
CHECK OUT
46
ORGANIC POLYMERS
THE SYNTHESIS OF NYLON AND THE IR ANALYSIS OF POLYMERS
Objective
The purpose of this experiment is to synthesize the polymer, Nylon-6,10, and to
determine the identity of an unknown polymer using infrared spectroscopy.
Introduction
Polymers are very large molecules composed of repeating subunits called
monomers. Polymers can either be synthesized through addition reactions of alkenes or
via condensation reactions. In addition reactions, the carbon-carbon double bond within
the alkene is broken and a new covalent bond between the two monomers is formed. In
the second type of reaction, two monomers condense together to form the polymer and
water as a by-product. In this experiment, Nylon-6,10 (an amide) will be synthesized by
reacting an amine with an acid chloride.
Nylon-6,10 is a polyamide formed from the reaction of a diamine, an amine that

has an NH2 group at each end, with a diacid chloride, which has a COCl group at each
end. Nylon-6,10 is named based on the structure of its amide monomer unit. The
diamine used is hexamethylene diamine, which consists of six carbons while the diacid
used is sebacoyl chloride, a component containing ten carbons. When the diamine and
diacid condense, HCl is formed as a by-product, which can cause undesirable side
reactions. As a result, the diamine is dissolved in a sodium hydroxide solution such that
it neutralizes the HCl as soon as it is formed.
Nylon is a very versatile substance. It is strong enough to be used in tires, but can
also be spun fine enough to be used in hosiery. It is also very durable as it washes and
dries easily, and holds shape well, which is why it is used in fabrics.
47
The identification of various compounds including polymers can be attained using

infrared (IR) spectroscopy. Since the absorption of infrared light can result in the
vibration of bonds, and the absorption of different bonds occurs at different frequencies,
the different functional groups present in the molecule can be identified from its IR
spectrum. IR spectroscopy is especially used in the waste management industry to aid
recyclers in identifying plastics that are missing their identification code. Plastics are
synthetic polymers that can be distinguished from each other based on the IR absorption
frequencies of the functional groups present in their monomeric units. In this experiment,
you will obtain the IR spectrum of an unknown synthetic polymer and confirm its identity
using Table 1.
Table 1: Structure of the Monomer Unit of Recycled Synthetic Polymers
Name of
Plastic
Identification
Code
Structure of monomer
Poly(ethylene
terephthalate)
Polyethylene
Poly(vinyl
chloride)
Polypropylene
Polystyrene
48
Procedure
Safety Precautions:
CAUTION: All chemicals, sodium hydroxide, sebacoyl chloride, and 1,6hexanediamine, are highly corrosive and are hazardous to skin and eyes. Safety gloves
and goggles must be worn at all times. All reagents should be kept and reacted in a
well ventilated fume hood.
Reagent Preparation
All glassware should be dry for steps 1 and 2.
1. Sebacoyl Chloride solution: Dissolve 1 mL of sebacoyl chloride (obtained from
the instructor) in 50 mL of hexane in a 250 mL beaker. Label the solution.
2. Diamine Solution: Dissolve 2.5 mL of 1,6-hexanediamine in 25 mL of a 3%
sodium hydroxide solution in another beaker. Label the solution.
Nylon Synthesis
3. Transfer 10 mL of the diamine solution into a clean, dry 150 mL beaker.
4. While holding the beaker containing the diamine solution at a slight angle, slowly
pour 20 mL of the sebacoyl chloride solution down the side of the beaker so that a
sebacoyl chloride layer is formed on top of the diamine layer.
5. With tweezers, grasp the polymeric film formed at the interface of the two layers
and slowly remove it from the beaker. Using a glass stirring rod, wrap the nylon
rope around it slowly turning the rod to remove more nylon from the beaker until
one of the reagents is exhausted.
6. Wash the nylon rope with 50 mL of distilled water and 20 mL of acetone.
7. Remove the rope from the stirring rod and blot dry between two pieces of large
filter paper.
8. Weigh the dried sample and record its weight. Calculate the percent yield.
9. WASTE: All chemicals should be disposed of in the waste container labeled
polymers in the hood. All glassware should be rinsed with plenty of water in the
hood.
IR Analysis
10. Obtain an unknown synthetic polymer from your instructor and record the
unknown number.
11. Run a background scan on the ATR-FTIR.
12. Load the sample and run the scan.
49
13. Label the peaks, and print the scan.

14. Based on the experimental absorptions, label the different types of functional
groups present, and report the identity of your unknown synthetic polymer.
Calculations
The percent yield of nylon can be determined by comparing the amount synthesized to its
theoretical yield.
Since there is a 1:1 ratio between each reactant and the nylon monomer unit, the moles of
each reactant can be converted to moles of monomer formed, to determine the limiting
reactant.
The volumes of each of the reactants can be converted to grams using the density of
sebacoyl chloride, 1.12 g/mL, and the density of 1,6-hexenediamine, 0.89 g/mL. The
mass of each reactant can then be converted to moles of the reactant, which can then be
converted to moles of the product. The moles of the product can be converted to grams of
the product by using the molecular weight of the nylon monomer unit, 282.43 g/mol.
50
Organic Polymers: The Synthesis of Nylon and the IR

analysis of Polymers
NAME________________
LOCKER #__________
DATE________________
LAB DAY AND
TIME_____________________
TITLE OF
EXPERIMENT____________________________________________
BALANCED EQUATION:
Part A: Synthesis of Nylon

Mass of Sebacoyl chloride reacted
Mass of 1,6-hexanediamine reacted
Theoretical yield of Nylon
Actual yield of Nylon
Percent yield of Nylon
Part B: Identification of Unknown Polymer

Unknown Number
Name of Polymer
IR Spectrum Data
Experimental
Absorption (cm-1)
Literature Absorption (cm-1)
Functional Group
present

Yield & Purity (30):_____ Post Lab Questions (10):_____ Lab Report Grade = ______
51
COLUMN CHROMATOGRAPHY
INTRODUCTION
Chromatography is an analytical technique that is used for the separation and
possible identification of different compounds. There are several types of
chromatography, such as liquid column chromatography, gas chromatography (GC), high
performance liquid chromatography (HPLC), and thin layer chromatography (TLC). The
next two experiments will demonstrate two of the different types of chromatography.
The next experiment deals with thin layer chromatography, today's experiment deals with
column chromatography.
A Russian biologist by the name of Tswett was the first to use column
chromatography. He used this technique to separate plant pigments that he was working
with. In today's experiment, we will use column chromatography to separate a 50-50
mixture of fluorene and fluorenone. The same factors that applied to separating
compounds in TLC also apply to column chromatography: the polarity of the solvent
(called the mobile phase), the polarity of the compounds to be separated, and the strength
of the absorbent (called the stationary phase). The absorbent that will be used in this
experiment is alumina and it will be packed into a column (we will use a buret as the
column). In the TLC experiment, alumina will be used as the absorbent.
Given the right conditions, no two compounds travel through the absorbent at the
same rate, therefore, a mixture of compounds can be separated. The moving compound
is attracted to polar sites on the absorbent which tend to keep the compound from moving
down the column. On the other hand, the compound also interacts with the mobile phase,
which moves the compound through the column. Depending on the polarity of the
compound, it will tend to associate either with the less polar mobile phase and move
more rapidly through the column, or with the more polar absorbent and travel more
slowly through the column.
The solvents used today are a mixture of petroleum ether (nonpolar) and acetone
(polar). Fluorene, which is less polar then fluorenone, will travel through the column
more rapidly. Fluorenone, the more polar compound, will travel through the column
more slowly.
* For a review of chromatography see:

Chromatography -- A Laboratory Handbook of Chromatography and Electrophoretic
Methods, 3rd ed., E. Heftman (Ed.), Van Nostrand Reinhold, New York, 1975.
52
PRECAUTIONS
1) Acetone and petroleum ether are very flammable. No flames today.
2) After the experiment, all solids from the column go into the pails, not in the sinks.
PROCEDURE
1) Work in pairs, put a plug of glass wool into the bottom of a clean, dry column,
followed by a small amount of sand (0.5 inches high), so that it sits on top of the glass
wool.
2) Fill 1/2 of the column with 2.5 % acetone /petroleum ether mixture (by volume)._
Hexane can be used in place of petroleum ether. You will need about 60-70 mL of the
2.5% acetone/petroleum ether mixture for the entire experiment, therefore, measuring out
this volume and keeping it in your graduated cylinder now, will save repeated trips to get
more later.
3) Fill the column half full with solvent. Weigh out 13g of alumina and add it slowly
through a dry, long stem funnel into the column. Tamp the column with rubber tubing to
make sure that the column has been packed well. The solvent level must remain above
the alumina at all times. Place a small amount of sand on top of the column (0.5 inches
high). After all the alumina has been added, open the column and let the solvent drain
out until the level of liquid is about 1/4 to 1/2 inch above the alumina. The solvent that
was collected can be reused later.
4) Weigh out 0.3 g of the 1:1 mixture of fluorene and fluorenone into a test tube and
dissolve this 1:1 mixture in 1 mL (20 drops) of toluene. Add this solution using a long 9
glass pipet carefully onto the column (as directed by your instructor) that contains a level
of solvent that is just above the alumina. The mixture should be added so that the liquid
drips directly on top of the column, not on the walls of the glass. Open up the stopcock
and again drain off solvent until its level is 1/4 inch above the alumina. Now fill the
column with solvent.
5) Secure six 50 mL Erlenmeyer flasks, mark them 1-6. Premark the flasks for 10 mL
volume using a permanent marker. Open the stopcock and allow the solution to drip
from the column into a 50 mL Erlenmeyer flask. Be sure to add more of 2.5 %
acetone/petroleum mixture to the top of the column so that the liquid level never goes
below the solid alumina level. After collecting about 10 mL wash the tip of the buret with
solvent into the flask When you have collected about 60 mL or when the yellow
fluorenone band is no longer visible (which ever occurs first), the chromatography is
complete.
53
6) Clean the column by using your forceps to remove the glass wool. Attach one end of
a hose to an air jet and the other end to the top of the column. With the bottom of the
column directed into a pail, gently turn on the air to push out all of the solid. No solids
should go into the sink. Rinse out the column with water and then dry it with a small
amount of acetone. Return the column to the front desk.
7) Check the purity of the six fractions using thin layer chromatography as described on
page 79 of your lab manual. Use 5% acetone/hexane as your solvent for TLC and use
aluminum oxide plates. In your notebook record which fractions are pure fluorine and
fluorenone and determine the Rf retention values for these two compounds. Next week
after the solvent has evaporated record the color of each fraction. Show the results to your
instructor. Time permitting obtain melting point of the pure fractions.
54
SYNTHESIS OF 1,4-DI-T-BUTYL-2,5DIMETHOXYBENZENE
INTRODUCTION
This synthesis is an example of an Electrophilic Aromatic Substitution reaction. The
direct alkylation of dimethoxybenzene, which contains the two strongly activating
methoxy groups. The methoxy group is an ortho, para director, therefore, the phenyl ring
of dimethoxybenzene will be alkylated exclusively at the ortho position. Since there are
two strongly activating groups the alkylation proceeds easily with sulfuric acid, a Lewis
acid catalyst. The alkylation involves the aromatic benzene derivative attacking the
electrophilic trimethylcarbocation.
PRECAUTIONS
1) Concentrated sulfuric acid is very corrosive, avoid contact with skin or clothes. If any
gets on your body immediately wash with a lot of water to remove the acid.
2) Several steps in the procedure are highly exothermic, therefore, following the
directions exactly as written.
* Williamson, K. L., Organic Experiments, 9th Edition, p.318.
55
PROCEDURE
1) Place 3 g. of 1,4-dimethoxybenzene, 5 mL of t-butyl alcohol, and 10 mL of glacial
acetic acid into a clean, dry 125 mL Erlenmeyer flask. Swirl the mixture and cool in ice
water bath to 0-3C.
2) Place 20 mL of concentrated sulfuric acid, in a beaker and cool in an ice bath for 15
minutes.
3) The cooled conc. sulfuric acid is placed into a separatory funnel and added dropwise
into the 125 mL flask over 4 -7 min with stirring.
4) The 125 mL flask is removed from the ice bath and the temperature is maintained at
20-25 C for 5 minutes.
5) Cool the 125 mL Erlenmeyer in ice bath again and add approximately 40 mL of ice
with stirring, (cool water ice-water bath). Stir thoroughly for 5 minutes. Add very
slowly 40 mL of ice cold water (there will be an exothermic, due to heat of reaction).
Continue to stir for a few minutes.
6) Filter out the 1,4-di-t-butyl-2,5-dimethoxybenzene with suction and (turn off the
vacuum) wash the solid in the Buchner funnel with two times 20 mL of cold water and
two times 15 mL of methanol.
7) Place a dry piece of filter paper on top of the solid and press down with a glass
stopper. Keep the vacuum filtration on for more than 15 minutes. No water should be
escaping from the Buchner funnel at this point. Carefully break up the cake in the
Buckner funnel and let the product sit in the funnel for an additional 15 minutes.
8) Obtain a weight of your crude product.
9) Recrystallize with 20 mL of methanol, using a 50 mL round bottom flask and a thin
condenser. After heating to dissolve the crystals, remove the heat and let the flask air
cool, then cool with an ice bath, filter solid and dry on Buckner funnel. If necessary use
additional 1-2 mL of methanol to transfer any remaining crystals that are in your 100 mL
RBF. Place crystals in 100 mL beaker.
10) Obtain weight and mp the following lab period.
56

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

57
THE CANNIZZARO REACTION

O
C
O
H
+ NaOH
CH2OH
H2O
O Na
Benzaldehyde
Benzyl alcohol
Sodium Benzoate
O
C
OH
Benzoic acid
Introduction
Benzaldehyde has no alpha hydrogens. Therefore, in the presence of a
concentrated basic solution, benzaldehyde can undergo self-oxidation and self-reduction
to yield a mixture of benzyl alcohol and the salt, sodium benzoate, which can then be
acidified to give the corresponding carboxylic acid, benzoic acid. This reaction is called
the Cannizzaro Reaction, named after the Italian chemist, Stanislao Cannizzaro. In 1853,
he was the first one to recognize that half of the benzaldehyde was oxidized to benzoic
acid and the other half was reduced to benzyl alcohol.
You will be isolating and purifying both the benzyl alcohol and the benzoic acid, so it
is necessary to calculate a theoretical yield for both of these products. You will be
determining percent yield for each product using separate Pre-Lab sheet. Be sure to
prepare two Pre-Lab data sheets using the complete overall reaction for each data sheet.
PRECAUTIONS
1) Be careful with the NaOH, it will burn the skin. Please clean up any pellets that might
spill in the hood or on the balances.
2) Do not inhale or spill the benzaldehyde on yourself. Wash it off with plenty of water
if you do spill it.
3) Ether is very flammable. No flames are to be used at anytime during the lab period
that ether is used.
4) Be careful with the hydrochloric acid, it also burns the skin. Wash it off with plenty of
water if it is spilt on you.
* Cannizzaro, S., Ann., 1853, 88, 129.
58
PROCEDURE
PART I
1) Add 15 mL of 50 % sodium hydroxide solution to a dry 125 mL Erlenmeyer flask.
2) Add 15 mL of benzaldehyde (15.7 g) to the flask and loosely cork it. Swirl the flask
for two to three minutes. Be careful, the flask gets hot.
3) Let the flask air cool and then put the corked flask in your locker until next period.
PART II
NO FLAMES TODAY!
1) Add 75 mL of hot water to the solid in the 125 mL Erlenmeyer flask. Stir until all of
the solid dissolves. This usually takes 10 to 15 minutes. Do not poke at the solid with
the stirring rod, you might break the flask.
2) Cool the solution in an ice/water bath to below room temperature.
3) Transfer the solution from your flask to your separatory funnel and add 25 mL of
ether. Invert and vent the funnel several times, inverting more often at the end.
4) Let the contents of the funnel settle for 30 seconds and then drain off the lower layer
into a 400 mL beaker (this contains the sodium benzoate dissolved in water). Pour the
top layer into a 250 mL beaker (this contains the benzyl alcohol dissolved in the ether).
5) Put the bottom layer, which is in your 400 mL beaker, back into the funnel and add
another 25 mL of ether. Invert and vent the funnel several times.
into the 400 mL beaker and save it, you will use it in step 9. Pour the top layer into the
250 mL beaker from step 3 that contains the top layer from that step.
7) Working with the beaker that contains the benzyl alcohol in the ether (the top layers),
add a spatula full of sodium sulfate to the flask to dry it and then decant the liquid
through your long stem funnel, that has a small piece of glass wool, into a 100 mL RBF.
8) Set-up a simple distillation (Figure 3, page 96) use a flask heater and a controller.
Pack the receiving flask in a beaker of ice/water. Using a low setting on the controller,
distill over the ether at a rate of one drop/second. Use your 50 mL RBF as a receiving
flask. When the distillation stops, increase the setting on the controller. You are done
distilling when no more ether distills over. Place the ether (in the 50 mL RBF) into the
container labeled "Recovered Ether" which is found in the hoods. You want to save the
benzyl alcohol that is still in the 100 mL RBF. Put the uncovered flask in your locker
until next period. You will only have a few mL of liquid left in your 100 mL flask.
59
9) Add enough 6 M HCl to the beaker from step 5 that contains the lower layer so that
the pH is 1 to 2. This usually requires about 70 mL. Stir for two minutes and then check
the pH with pH paper. You should see a thick white solid precipitate out at this point. It
is benzoic acid. Cool this mixture in an ice/water bath.
10) Vacuum filter the benzoic acid mixture. Put the benzoic acid into a 600 mL beaker
until next period.
PART III
1) Transfer the benzyl alcohol from the 100 mL flask to a 25 mL RBF, set up a simple
distillation (Figure 3, page 96) using the 25 mL flask as the distilling flask a 50 mL
receiver and a temperature probe. Remember to properly adjust the position of the
temperature probe so that it reads the temperature of the vapor. Add a fresh boiling chip
to this flask. Using a flask heater, collect from 190 to 206C as pure benzyl alcohol. If
liquid distills over before 190C, change the receiving flask at 190C. Hand in the pure
benzyl alcohol today in a small sample bottle with the usual label. Benzyl alcohol is a
clear, colorless liquid. If the temperature drops increase the setting on the controller.
2) Working with the solid benzoic acid in the beaker, add 350 mL of water and a spatula
full of charcoal to the benzoic acid. You will now recrystallize the benzoic acid. Review
the recrystallization technique on pages 7 and 93.
3) Heat the beaker on a wire gauze with a flame until the mixture starts to boil. At the
same time you should be preheating your powder funnel with steam. Do not breath in the
vapors of the boiling mixture. With a large piece of filter paper folded into the hot
powder funnel, pour the boiling mixture in the 600 mL beaker through the powder funnel
and collect the liquid into a 400 mL beaker. The 600 mL beaker is hot so use a "Hot
hand" to grab it. Turn off the flame when grabbing the 600 mL beaker. While the hot
mixture is being filtered through the powder funnel, keep the rest of the contents of the
600 mL beaker near boiling by heating it gently with a flame.
4) Cool the 400 mL beaker in an ice/water bath until the entire contents of the beaker is
has cold as the ice/water. You should see the benzoic acid precipitate out at this point,
stir.
5) Vacuum filter the benzoic acid mixture and put the solid benzoic acid into a clean, dry
100 mL beaker until next lab period.
60

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

61
SPECTROCOPY
INTRODUCTION
The determination of the structure of an organic compound is a very important
aspect of organic chemistry. It is routinely performed in organic laboratories by the use
and interpretation of physical and spectral data.
The ELEMENTAL ANALYSIS of a pure unknown organic compound will give
you the percentage of each element present in that compound. If your unknown contains
oxygen, its percentage is not given, and the sum of all the percentages given will not
equal 100. If this is the case, you must subtract your total percentage from 100 to get the
percentage of oxygen in your unknown. After you know the percentage of each element,
you can calculate the EMPIRICAL FORMULA. For a review of how to do this, please
refer to chapter 1 (p.20-21) of your lecture text, Organic Chemistry by L. G. Wade Jr..
The MOLECULAR WEIGHT (MW) of your unknown can be determined by
MASS SPECTROSCOPY (MS). Knowing the molecular weight and the empirical
formula, you can calculate the MOLECULAR FORMULA.
The INFRARED (IR) SPECTRUM of your unknown will help you to identify the
different functional groups that are present in your unknown. To review IR, see chapter
12 of your lecture textbook. Looking at your IR spectrum, you can determine the
wavenumber of the major peaks. Compare these wavenumbers to the list of
wavenumbers in Table 1. You can then determine what functional groups are present in
your unknown compound.
The CARBON 13 NUCLEAR MAGNETIC RESONANCE (13C NMR) spectrum will
tell how many different types of carbon atoms are present in your unknown compound.
The number of signals in the spectrum is equal to the number of different types of carbon.
Table 2 lists some types of carbon and where a signal will appear for that group.
The PROTON NUCLEAR MAGNETIC RESONANCE (1H NMR) spectrum is very
useful in determining the structure of an organic compound. From this spectrum, several
pieces of information can be obtained.
a) The number of different kinds of hydrogen is determined by counting the number of
signals.
signal, see table 3.
c) The number of each kind of hydrogen is determined by comparing the area of each
signal to each other.
d) You can determine the neighboring protons by the splitting of each signal.
62
With some or all of this spectroscopic data, along with some physical data, such as,
melting point or boiling point, chemist can determine the structure of naturally occurring
compounds isolated from nature or compounds that have been synthesized in the
laboratory.
TABLE 1 - IR WAVENUMBERS (cm-1) AND CORRESPONDING
FUNCTIONAL GROUPS
WAVENUMBER
FUNCTIONAL GROUP
3600 - 3200
3500 - 3300
~3300
3100 - 3010
2970 - 2850
2850, 2750
2260 - 2190
2260 - 2190
1760 - 1690
1680 - 1500
1570-1500 and 1370-1300
1360 - 1180
1300 - 1050
O-H
N-H
C-H of alkyne
=C-H of alkene
-C-H of alkane
O=C-H of aldehyde
CN
CC
C=O
C=C
NO2
C-N
C-O
CLASS OF COMPOUND
alcohol, carboxylic acid
amine, amide
alkyne
alkene
alkane
aldehyde
nitrile
alkyne
aldehyde, ketone, ester,
carboxylic acid, amide
alkene, aromatic
nitro group
amine, amide
alcohol, ether, ester,
carboxylic acid
TABLE 2 TYPE OF CARBON

saturated carbon (sp3)
C=C (sp2)
TYPE OF CARBON
0 - 50
100 - 160
CC (sp)
C=O (sp2)
60 - 90
150 - 230
TABLE 3 TYPE OF PROTON

Saturated C-H
C=C-H
CC-H
Aromatic C-H
X-C-H (X = F,Cl,Br,I,O)
TYPE OF PROTON
0.2 - 1.5
4.6 - 5.9
2.0 - 3.0
6.0 - 8.5
2.0 - 4.5
O=C-C-H
O=C-H
-COOH
-N-H or -O-H
63
2.0 - 4.1
9.0 - 10.0
10.5 - 12.0
Variable (1.0 - 5.0)
PROCEDURE
You will be given the mass spectrum, IR, 1H NMR, 13C NMR, and some physical
properties of an unknown organic compound. From this information you will determine
the structure of the unknown compound.
1) Write down as much of the elemental composition that is given or can be deduced.
2) Calculate the empirical formula.
3) From the mass spectrum, determine the molecular weight.
4) Calculate the molecular formula.
5) Determine what bonds (functional groups) could be present based on the IR spectrum.
6) Based on the 13C-NMR information, how many different types of carbons are there?
7) Based on the 1H-NMR spectrum, how many signals are present? What is the delta
value of each signal, how many protons cause each signal, what is the splitting of each
signal (singlet, doublet, triplet, quartet, or multiplet), and how many neighboring protons
are causing this splitting?
8) Determine the m/z value of the base peak fragment and its structure?
9) Record your results in your notebook and then hand in your structure determination
data sheet and your spectra sheet during this lab period. Space is provided next to the
spectra to write out your answers after you have worked them out on scrap paper,
recorded them in your notebook and are confident in your conclusions. For the 1H-NMR
spectra, draw the structure and assign all of the protons to the correct corresponding
signal.
64
NAME_________________________
DATE ________________
STRUCTURE DETERMINATION DATA SHEET

1) ELEMENTAL ANALYSIS:
% C________
% H________
% __ ________
%__ _______
2) CALCULATION OF EMPIRICAL FORMULA (SHOW WORK)
EMPIRICAL FORMULA = __________________

3) MOLAR MASS = _____________
4) CALCULATION OF MOLECULAR FORMULA (SHOW WORK)
MOLECULAR FORMULA = _______________

5) IR DATA:
MAJOR PEAKS POSSIBLE FUNCTIONAL GROUP PRESENT

_________/cm
_______________________________________
_________/cm
_______________________________________
_________/cm
_______________________________________
_________/cm
_______________________________________
_________/cm
_______________________________________
FROM THE IR DATA, WHAT CLASS OF ORGANIC COMPOUNDS MIGHT YOU

HAVE?
65
6) CARBON 13 NMR DATA:

HOW MANY DIFFERENT SIGNALS DO YOU HAVE? ________
(THIS IS HOW MANY DIFFERENT TYPES OF CARBON ATOMS THERE ARE)
7) PROTON NMR DATA:

a) HOW MANY SIGNALS ARE THERE? ___________ (THIS IS HOW MANY
DIFFERENT HYDROGEN ATOMS IN YOUR UNKNOWN)
b)
VALUE
# OF PROTONS
SPLITTING
NEIGHBORING PROTONS
_________
________________
____________
_______________
_________
________________
____________
_______________
_________
________________
____________
_______________
_________
________________
____________
_______________
_________
________________
____________
_______________
8) WHAT IS THE m/z VALUE AND A POSSIBLE STRUCTURE FOR THE BASE
PEAK OF YOUR COMPOUND?
9) USING ALL OF THE ABOVE INFORMATION, DRAW THE STRUCTURE OF

YOUR UNKNOWN AND GIVE ITS IUPAC NAME.
66
SYNTHESIS OF BENZOPHENONE OXIME
H2N OH HCl + NaOH

Hydroxylamine
hydrochloride
C O
Ethanol
Water
H2N OH
H2N OH + NaCl + H2O

Hydroxylamine
Ethanol
Water
Benzophenone
C N OH +
H2O
Benzophenone
Oxime
Introduction
Several derivatives of ammonia will add to the carbonyl group of a ketone. The
product contains a carbon-nitrogen double bond resulting from the elimination of a
molecule of water from the initial addition product.
In today's experiment, the ketone used will be benzophenone. The ammonia
derivative will be hydroxylamine. Hydroxylamine is basic and will react with
hydrochloric acid to form the salt, hydroxylamine hydrochloride. This salt is less easily
oxidized by air than the free base, so it is easier to handle and has a longer shelf life. The
salt is converted back into the free base, hydroxylamine, with the addition of sodium
hydroxide.
PRECAUTIONS
1) The recrystallization of benzophenone oxime is done in ethanol, therefore, it must be
heated with a flask heater. No flames are to be used during this part of the experiment.
2) Be careful with the sodium hydroxide and sulfuric acid solutions, they will burn.
* Lachman, Org. Syn., 1930, 10, 10.
67
PROCEDURE
1) Clamp a 100 mL RBF to a ring stand and add 2.7g of benzophenone and 3.0g of
hydroxylamine hydrochloride using your powder funnel.
2) Add 40 mL of ethanol and then 25 mL of 20 % sodium hydroxide solution to the 100
mL RBF. Swirl the flask to mix its contents. There will still be some undissolved solid
at this point.
3) Reflux (add boiling chips and use grease) (Figure 2, page 94) for 10 minutes. Use a
flask heater and let the solution boil gently during this time. After heating for a few
minutes, all of the solid should dissolve.
4) Cool the flask in an ice/water bath, then transfer its contents to a 150 mL beaker and
acidify the filtrate by adding enough 20 % sulfuric acid (about 20 mL) so that pH paper
indicates that the mixture is pH 1 or 2. You should see the oxime precipitate out at this
point. Stir and cool in an ice/water bath for 5 minutes.
7) Collect the solid benzophenone oxime with vacuum filtration. Wash the solid with
four times of 20 mL of water. Place filter paper on top of the cake, press on cake with
hollow stopper for15 minutes. Remove solid and spread out on large filter paper. With
spatula make solid into a fine powder. Allow to dry for 15 minutes in hood. The weight
of crude should be 2.-2.5 g.
8) Put the solid into a 50 mL round bottom flask with approximately 10 mL of ethanol
and thin condenser. Heat the beaker gently with a flask heater for 5 minutes or until the
solid dissolves. You should be stirring during this step. Cool with an ice/water bath.
Then filter using dry filtration equipment. Mat down the filter paper with ethanol. Use 12 mL of additional ethanol to remove any crystals remaining in your flask.
9) Let the recrystallized product dry in a 100 mL beaker in your locker until next lab
period.
NOTE: Always use the filtrate (the liquid in the filter flask) to wash out any solid that
did not pour into the Buchner funnel.
68

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

69
THE REARRANGEMENT OF BENZIL

O O
C C
+ KOH
1) H2O, EtOH
2) HCl, ice
O
C C OH
OH
Benzilic acid
Benzil
INTRODUCTION
As the title of this reaction indicates, a rearrangement takes place. Specifically, a
phenyl group with a pair of electrons migrates to the adjacent carbon. Can you write out
the mechanism for this reaction?
PRECAUTIONS
1) Be careful with the potassium hydroxide pellets. If you spill any pellets in the hood,
stop and clean them up.
2) Be careful with the concentrated hydrochloric acid.
* Hans V. Liebig, Ber., 1908, 41, 1644 - 1645.
70
PROCEDURE
1) In a 100 mL RBF add 2g of benzil, and 20 mL of 10% KOH that is a mixture of
ethanol and water.
2) Gently reflux (Figure 2, page 94) with a flask heater and controller for 15 minutes.
3) Let the reaction mixture air cool for a couple of minutes, add 50 mL of water and a
small spatula full of charcoal, and then stir for several minutes.
4) Vacuum filter this mixture, the solid that is filtered out on the Buchner funnel can be
discarded. The potassium salt of benzilic acid is dissolved in the filtrate, therefore, save
the filtrate.
5) Add approximately 25 g of ice and 8.5 mL of concentrated hydrochloric acid to your
250 mL beaker. Slowly add the filtrate to this acid/ice mixture with constant stirring.
Continue to stir and cool this mixture for several minutes after all of the filtrate has been
added.
6) Vacuum filter the benzilic acid mixture.
7) Add all of the solid benzilic acid and 125 mL of hot water to your 250 mL beaker.
Place this mixture on your wire gauze and heat to boiling with a flame. Let this mixture
gently boil for several minutes, stirring frequently. Pour this boiling solution through a
powder funnel that contains a large mat of glass wool and collect the filtrate in your 400
mL beaker. Gently push down on the glass wool with a spatula to get most of the water
to drain into the beaker. After collecting all of the filtrate, cool it in an ice/water bath
until it is ice cold. Occasionally stir the liquid while it is cooling. Isolate the purified
benzilic acid by vacuum filtration.
8) Let the solid dry in a 100 mL beaker until next week.
71

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM
Product Coeffc.
b
Moles Reactant
Coeff.
Moles d
Produc
of
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

72
PREPARATION OF METHYL BENZOATE

O
COOH
+ CH3OH
Benzoic acid
H2SO4
Methanol
OCH3
+ H2O
Methyl benzoate
INTRODUCTION
Esters, for example methyl benzoate, can be synthesized by refluxing a carboxylic
acid and an alcohol. This reaction, called the Fischer Esterification, is catalyzed by a
concentrated mineral acid, such as, sulfuric acid. As you can see from the above
equation, water is produced. This water will hydrolyze the ester back to the starting
materials, therefore, the equation is shown as being in equilibrium.
If you started with equal molar amounts of carboxylic acid and alcohol, the yield
of ester under equilibrium conditions should be about 67 %. This yield can be improved
by removing the water has soon as it is formed or by adding more of one of the starting
materials. In today's experiment, you will add excess alcohol to increase your yield.
PRELIMINARY CALCULATIONS
There is a report sheet for this experiment which shows how to calculate the
quantities of all reagents, based on weight of benzoic acid you obtained from the
Cannizzaro Reaction. These calculations must be done before you start this experiment.
PRECAUTIONS
1. Unless otherwise specified, all glassware should be clean and dry.
2. Both methanol and ethyl ether are flammable, therefore, no flames today.
3. Use care when handling concentrated sulfuric acid, it burns.
* Fischer, E.; Speier, A., Ber., 1895, 28, 3252 .
73
PROCEDURE
1. Place the benzoic acid (use at least 5g of benzoic acid) and then the methanol in a 100
mL round bottom flask (RBF).
2. Carefully pour the concentrated sulfuric acid down the side of the flask, swirl to mix,
add two boiling chips and attach the reflux condenser.
3. Using a flask heater and controller, reflux (Figure 2, page 94) the reaction mixture for
30 minutes. During the reflux, prepare the glassware needed to complete this experiment
and hand in the benzilic acid from the previous experiment.
4. With the condenser still attached, place the flask in a beaker of ice water, cool to
below room temperature, and transfer the liquid to your separatory funnel. Rinse the 100
mL RBF with 50 mL of water and add this rinse water into your separatory funnel.
5. Add one half of the calculated ethyl ether to your separatory funnel. (If your
calculated ether volume is under 10 mL, see your instructor.) Ethyl ether has a very low
boiling point (37C) and thus has a high vapor pressure at room temperature, therefore,
frequent venting of the separatory funnel is necessary. As the pressure in the funnel
decreases, shake the solution vigorously (with continued venting) for 2 minutes This
washing with ether extracts the methyl benzoate into the upper ether layer.
6. Allow time for layer separation, collect the lower layer in a small beaker and place the
upper layer in a 125 mL Erlenmeyer flask. Put the lower layer back into the separatory
funnel with the remaining ether and repeat the extraction. This time the lower layer can
be discarded in the waste container and the upper ether layer added to the first upper layer
in the Erlenmeyer flask.
7. Clean your separatory funnel (it does not have to be dry) and add the combined ether
extracts that is in your 125 mL Erlenmeyer flask. Carefully add 25 mL of 10% sodium
carbonate solution, do not stopper, but swirl the mixture for one minute. Now stopper the
funnel and with frequent venting, shake the solution for 2 minutes. Allow separation,
collect the lower layer in a small beaker and check the pH. If basic, discard the lower
layer in the waste container; if not basic, repeat with fresh 25 mL portion of 10% sodium
carbonate solution until the lower layer checks basic.
8. Add 10 mL of saturated sodium chloride solution to the upper layer that remains in
your separatory funnel, shake and vent a few times, allow separation and discard the
lower layer in the waste container. Place the upper layer in a 125 mL Erlenmeyer flask,
add a small amount of sodium sulfate powder to dry it, cover the flask and prepare the
distillation setup.
74
9. Set up a simple distillation (Figure 3, page 96) with a flask heater. Distill from a 50
mL RBF with a 25 mL RBF packed in a small beaker of ice water as the receiving flask.
You can replace the thermometer with a glass stopper. Using a long stem funnel with a
small, loose plug of glass wool, decant the dry liquid from your Erlenmeyer flask and
distill off the ether; set the Heat Control low. Your methyl benzoate product is a
relatively high boiling liquid and will remain as the residue in your 50 mL RBF. The
distillate, ethyl ether, is to be collected and placed in the bottle labeled "Recovered
Ether".
10. Put the methyl benzoate in a vial unstoppered. Take an FTIR, identify the major
bands, and hand in the product next period.
75
NAME_________________________
DATE ________________
METHYL BENZOATE REPORT SHEET

PRELIMINARY CALCULATIONS
A. WEIGHT of BENZOIC ACID from Cannizzaro Rxn.__________g.
B. VOLUME of METHANOL: 2.5(A) = ____________ mL
C. VOLUME of CONC. SULFURIC ACID: 0.3(A) = __________ mL
D. VOLUME of ETHYL ETHER: 4.0(A) = _________mL

1. MOLAR MASS of BENZOIC ACID ___________ g./mole
2. MOLES of BENZOIC ACID USED ___________ moles
3. MOLAR MASS of METHYL BENZOATE ___________ g./mole
4. THEORETICAL YIELD of METHYL BENZOATE ___________ g.
DATA
a. BOILING POINT of METHYL BENZOATE (literature value) ________ C
b. ACTUAL YIELD of METHYL BENZOATE _________ g.
c. PERCENT YIELD ________ %
GRADING: Pre-Lab (20): _____ Experimental Technique (30):_____

Yield & Purity (30):_____ Post Lab Quiz (10):_____ Lab Report Grade = _____
76
SYNTHESIS OF LIDOCAINE
INTRODUCTION
Lidocaine a local anesthetic was first synthesized by a Swedish scientist Nils Lodfgren
in 1943, which he named Xylocaine. The drug is sold as the hydrochloride or sulfate salt
which are more stable and compatible with biological media. Lidocaine is prepared in
two steps the acetylation of 2,6-dimethylaniline with chloroacetylchloride to give the
amide, N-(dimethylphenyl)chloroacetamide ( chloroacetamide). Finally the
chloroacetamide can then be alkylated with diethylamine. To check on the purity of the
intermediate and product TLC is used.
PRECAUTIONS
Wear gloves in the first few steps of this reaction. Make sure that all your equipment is
absolutely dry during step 1 & 2 of procedure A and B. Since 2,6-dimethyl aniline is
toxic avoid contact with skin. Work with the chloroacetyl chloride under the hood at your
bench top. If the vapors come in contact your eyes or mouth, it will act as a lachrymator.
This will cause severe breathing and eye irritation. In the hood, rinse out any container
that was used to measure out the chloroacetylchloride with plenty of water. Glacial acetic
acid is corrosive and can cause breathing and eye irritations.
* Lofgren, N. M.; Lundquist, B.J. Alkyl Glycinanilides. U.S. Patent 2,441.498, May 11,
1948.
77
PROCEDURE
Parts I & II
Part II
1) Place 3 mL (2.9 g.) of 2,6-dimethylaniline and 15 mL glacial acetic acid into a clean,
dry 250 mL Erlenmeyer flask. Swirl the mixture.
2) Add 2 mL (2.85 g.) of chloroacetylchloride and swirl vigorously. Exotherm.
3) Quickly add 25 mL of sodium acetate solution (54 g sodium acetate in 100 mL water).
Swirl the flask. Be sure that the vent hood is pulled down as far as possible. The flask
will get warm and smoke will come out of the flask. Hydrochloric gas is generated during
the reaction.
4) Add 60 mL of cold water (cool water ice-water bath). Stir thoroughly.
5) Filter out the N-(2,6-dimethylaniline) chloroacetanilide with suction and (turn off the
vacuum) wash the solid in the Buchner funnel with 50 mL of cold water in small
portions.
6) Place a dry piece of filter paper on top of the solid and press down with a glass
stopper. Keep the vacuum filtration on for more than 5 minutes. No water should be
escaping from the Buchner funnel at this point. Carefully break up the cake in the
Buckner funnel and let the product sit in the funnel for an additional 5 minutes.
7) Obtain a weight of your product. Save enough sample to get a melting point and a
TLC.
Part II
1) Place N-(2,6-dimethylaniline) chloroacetanilide, 30 mL of toluene, and magnetic
stirring bar into a clean, dry 100 mL RBF.
2) Add 7.5 mL ( 5.29 g.) of diethyl amine ( this chemical smells be sure to pull down the
vent hood) to the flask, attach a reflux condenser, and turn on the water.
3) Heat the flask with a flask heater (setting should be 30) under reflux for 1 hour. Allow
to cool to room temperature. Remove magnetic stir bar and return it to the instructor.
Pour the reaction product into bottles with parafilm between the cap and bottle. Finish in
the next lab period.
78
Part III
4) Transfer the solution from your flask to your separatory funnel and add 50 mL of
water. Invert and vent the funnel several times, inverting more often at the end.
into a 400 mL beaker. Add 50 mL of water. Invert and vent the funnel several times,
inverting more often at the end. Drain off the lower layer into the 400 mL beaker. Add 50
mL of water , repeat extraction and drain. Add another 50 mL repeat extraction and drain.
6) Add 20 mL of 3M HCl to separatory funnel, shake and collect HCl water layer in a
250 mL Erlenmeyer flask. Save HCl water layer!!!
7) Add 20 mL of water to separatory funnel, containing top toluene layer, shake and
collect the lower, water layer, also in the 250 mL Erlenmeyer flask. Combined two
aqueous layers cool in ice-water bath. The upper toluene layer discard in Organic
hazardous waste container.
8) Add 5 mL portion of 10% sodium hydroxide to aqueous layer. Swirl and check pH
with pH paper. Continue to cool in ice-water bath. Add sufficient amount of 10% sodium
hydroxide until solution is basic. Should be about 20-25 mL.
9) The flask should sit in ice-water bath for additional 5-10 minutes. Continue to swirl.
10) Filter out the Lidocaine with suction and (turn off the vacuum) wash the solid in the
Buchner funnel with 25 mL of cold water in small portions.
11) After all the water has been removed place a dry piece of filter on top of solid and
press down with glass stopper. Keep vacuum on for an additional 5 minutes.
12) Place solid in a 150 mL beaker allow to dry until the next lab period.
Thin Layer Chromatography
Thin Layer Chromatography, TLC, is a simple rapid and inexpensive type of
chromatography. In TLC, a glass or plastic plate that is coated with a thin layer of an
absorbent (called the stationary phase) is spotted with the compound or mixture to be
analyzed. A suitable solvent (called the mobile phase) is allowed to ascend the layer of
absorbent by capillary action. This mobile phase is the transport medium for the
compounds that are to be separated. The movement of compounds during TLC is the
result of three factors.
1) The strength of the stationary phase (absorbent)
2) The polarity of the mobile phase (solvent)
3) The polarity of the compound (solute) to be separated.
79
Given the right conditions, no two compounds travel up the absorbent at the same
rate; therefore, a mixture of compounds can be separated. The moving compound is
attracted to polar sites on the absorbent, which tend to keep the compound from moving
up the plate. On the other hand, the compound also interacts with the mobile phase,
which moves up the plate. Depending on the polarity of the compound, it will tend to
either associate more with the mobile phase and move higher up the plate, or the
compound will associate more with the absorbent and travel more slowly up the plate.
In TLC, the distance that the compound travels up the plate is compared to the
distance that the mobile phase travels. This ratio of compound movement to solvent
movement is called the Rf value for that particular compound. Every compound, given
the right conditions, has its own characteristic Rf value. Therefore, the Rf value of an
unknown compound can be compared to the values of known compounds to identify the
unknown compound.
In todays experiment, you will determine the Rf values of N-(dimethylphenyl)chloroacetamide and Lidocaine and a mixture using silica gel as the stationary phase and
hexane ethyl acetate as the mobile phase. These samples are dissolved in acetone and
provided in the fumehood. Afterwards, you will also run a TLC of both your crude and
pure product from the previous experiment and compare these Rf values to the known Rf
values of the N-(dimethylphenyl)chloroacetamide and Lidocaine. If the Rf values of
your reaction products are the same as the Rf values of the known N(dimethylphenyl)chloroacetamide and Lidocaine, then you have identified your reaction
products.
When separating a mixture of two or more compounds using TLC, the Rf value for
each compound must be calculated. In todays experiment, the compounds to be
separated are not visible unless they are subjecting the plate to UV light or Iodine.
In order to obtain successful results it is important that one uses a small amount of sample
in the procedure. This may require some trial and error to determine the proper
conditions. However, this process is brief and can be easily adjusted and repeated.
PROCEDURE (Bring a pencil and ruler to class)
1) Add a piece of large filter paper to two clean, dry TLC chambers. You will have to
cut the filter paper so that it fits properly and you can see through one side of the
chamber.
2) Add 50 % hexane, 50 % ethyl acetate mixture to each chamber and cover; this will be
enough for the whole experiment.
3) In three separate vials place of N-(dimethylphenyl)chloroacetamide, and Lidocaine
and the mixture these solution are already diluted in acetone. * If these solutions are too
concentrated you will get very poor results. Cover the vials.
80
4) Draw a line one centimeter from the top and bottom of the TLC plate. Use a pencil
and draw on the silica gel side. Do not press to hard with the pencil. Label the plates on
top when doing the next step. Spot the samples in the center
5) Using the prepared capillary tubes, on the first plate, place a small (1-2 mm in
diameter) spot of the N-(dimethylphenyl)chloroacetamide solution on the line on the left
side. Spot the mixture N-(dimethylphenyl)chloroacetamide, and Lidocaine on the line in
the center of the plate and the Lidocaine solution on the right side. On the second plate,
spot the solutions of the two products on the line, one near the left side and the other near
the right side. Remember to label the plates. Dont spot samples close to the edge of the
plate.
6) Place the one plate with the knowns into one of the TLC chambers, and the product
plate in the other TLC chamber. (You may want to wait a minute or two between
inserting the two plates) Put the top back on the chambers. Do not disturb or move the
chambers on the bench top. Begin observing the movement of the spots up the plate
wall. Notice that the solvent is saturating the plate surface.
7) Before the solvent front reaches the top of the plate, ( you may have to remove the
cover briefly to check) remove the plate from the chamber with tweezers and place it on a
piece of paper in your hood. Quickly mark where the solvent front stopped. If the
solvent front is already at the top, discard and repeat. If there is a trail underneath
the developed spot, your solutions are too concentrated. The solutions must be
diluted and the plate repeated.
Place the TLC plate in the UV chamber (set the switch) using short wave UV light,
mark a circle around the peaks that are observed. Then place in Iodine chamber.
Remove the plate with forceps. Are there any changes?
8) Measure, in cm, the distance that the compound moved, by measuring from the line to
the center of the developed spot. Divide it by the distance that the solvent moved (from
the line to the mark on top) to calculate the Rf value for the compound. Two spots;
calculate two Rf values.
Mark detailed drawings of the two plates in your notebook and discard the plates as
directed.
9) Based on the Rf values, identify your reaction products (the crude and the pure),
Record the calculated Rf values for all spots in your notebook and on the data sheet,
which should be handed in today.
10) Remove the filter paper from the chambers and discard the paper in a separate
identified waste container. Return the chambers with the caps off to the boxes in the
reagent hood. Discard in the general organic waste container.
81

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

82

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

83
THIN LAYER CHROMATOGRAPHY DATA SHEET
COMPOUND
Rf VALUE
1) N-(dimethylphenyl)chloroacetamide
2) Lidocaine
_________
3) Mixture
__________ and __________
_________
4) Reaction Product
___________________________
N-(dimethylphenyl)- chloroacetamide
5) Reaction Product
Lidocaine
___________________________
My reaction product Lidocaine __________________________________

Consists of
Draw your plates below, showing the distances in centimeters. Identify each plate.
84
SYNTHESIS OF DIBENZALACETONE
(Also called Dibenzylideneacetone or 1,5-diphenyl-1,4-pentadien-3-one)
O
O
C
O
H
+ CH3
Benzaldehyde
CH
CH3
NaOH
Ethanol
CH
CH
CH
Dibenzalacetone
Acetone
+
2 H2O
Introduction
Today's experiment is an example of a crossed aldol condensation. Because one
of the reagents in this reaction is benzaldehyde, which contains no alpha hydrogens and
can not condense with itself, a good yield of dibenzalacetone is expected.
Dibenzalacetone is a yellow solid. This yellow color is due to the highly conjugated
system in dibenzalacetone (alternating double and single bonds).
PRECAUTIONS
1) Be careful with the sodium hydroxide solution, it will burn the skin.
* Schmidt, Ber., 1881, 14, 1460 .
85
PROCEDURE
1) Place 3.0 mL (3.15g) of benzaldehyde, 1.0 mL (.791g) of acetone and 20 mL of
ethanol into a 250 mL beaker. Stir.
2) Now add 25 mL of 10 % sodium hydroxide solution to the 250 mL beaker and stir for
about 20 to 25 minutes. You should see a yellow solid forming during this time.
3) Vacuum filter the contents of the beaker and wash the solid in the Buchner funnel
with 2 x 50 mL of water.
4) Wash the solid in the Buchner funnel with 25 mL of 4 % solution of acetic acid in
ethanol without the vacuum on. (If the solution is not already made for you, mix 1 mL of
concentrated acetic acid with 24 mL of ethanol in a beaker) After one or two minutes,
turn on the vacuum and let all the liquid drain out of the Buchner funnel. Do not get
alarmed if you see some solid in your filter flask, it is to be discarded as directed by your
instructor.
5) Purify the dibenzalacetone by putting it into a 50 mL RBF with 10 to 15 mL of
ethanol. Clamp the beaker to the ring stand and very gently heat the flask with flask
heater for 5 minutes or until all of the solid dissolves. Stir the contents of the beaker
during the heating. At the end of 5 minutes or when all of the solid dissolved, cool the
flask in ice/water until it is cold.
6) Stir the contents of the flask for one minute and then vacuum filter, all equipment
should be clean and dry (no acetone or water in the equipment). Mat down the filter
paper with a small amount of ethanol, not water. Let the dibenzalacetone dry in a 150
mL beaker until next lab period. Take an FTIR of your product after it has dried.
86

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Product Coeffc.
a
Grams MM Molesb Reactant
Coeff.
Moles d
Produc
of
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

87
-D-(+)-GLUCOSE PENTAACETATE
CH2OH
CH2OAc
+ 5 CH3 C O C CH3
OH
HO
OH
Acetic anhydride
OH
a-D-(+)-Glucose
OAc
OA
c
OAc
b-D-(+)-Glucose pentaacetate
O
Ac =
O OAc
NaOAc
+
5 CH3COOH
Acetic acid
C CH3
Acetyl group
INTRODUCTION
It is interesting to note that in this reaction, the hydroxyl group on the number one
carbon of glucose is in the alpha position, yet the acetyl group in the glucose pentaacetate
is in the beta position. This inversion of configuration between reactant and product is
catalyzed by the addition of sodium acetate. With sodium acetate, a basic catalyst, the
beta pentaacetate predominates because sodium acetate catalyzes the interconversion of
alpha and beta glucose, but not the pentaacetates, and the rate of acetylation of beta
glucose is much faster than that of the alpha isomer.
PRECAUTIONS
1) Work with the acetic anhydride under the hood at your bench top. If the vapors come
in contact with the moisture from your eyes or mouth, the acetic anhydride will react with
that moisture to produce acetic acid. This will cause severe breathing and eye irritation.
In the hood, rinse out any container that was used to measure out the acetic anhydride
with plenty of water.
2) The formation of glucose pentaacetate is an exothermic reaction, therefore, the heating
of this reaction must be done very carefully. Follow the directions in the procedure
exactly.
* Erwig and Koenigs, Ber., 1889, 22, 2207 .
88
PROCEDURE
1) Place 1.0g of D-(+)-glucose and 0.6g of sodium acetate and 2 boiling chips into a
clean, dry 50 mL RBF.
2) Add 5.0 mL (5.4g) of acetic anhydride to the flask, attach a reflux condenser, and turn
on the water.
3) Heat the flask with a low flame (use your wire gauze). You should be constantly
rocking the ring stand so that the contents of the flask are swirling. As soon as the liquid
in the flask starts to boil, turn off the flame. Continue to swirl the flask until the liquid
stops boiling. You should see no solid in the flask at this time.
4) Pour this hot reaction mixture into a 250 mL beaker that contains 40 mL of cold water
with some chips of ice in it. You should be stirring the water while adding the reaction
mixture to it. Stir until a lot of solid precipitates out of solution and all of the ice melts.
You must keep stirring until you see solid and it is not sticky.
5) Filter out the glucose pentaacetate with suction and wash the solid in the Buchner
funnel with 10 mL of cold water.
6) Transfer all of the filtered solid to your 400 mL beaker and add a small spatula full of
charcoal and 150 mL of water.
7) Recrystallize (Figure 1, page 93) the glucose pentaacetate by boiling the mixture in
the 400 mL beaker and then pouring it through a preheated powder funnel that contains a
folded piece of filter paper.
8) Cool the filtrate in ice/water and then filter out the pure glucose pentaacetate with
suction.
9) Let the solid dry in a large beaker until next lab period.
89

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

90
CHECK OUT
91
THE SYNTHESIS OF ASPIRIN
OH
+
C OH
O
Salicylic Acid
O
CH3
O
CH3
O C CH3
C OH
O
Acetylsalicylic Acid
Acetic Anhydride
O
CH3
C OH
Acetic Acid
Introduction
It has been known for centuries that an extract from willow leaves and bark
possessed pain-relieving (analgesic) and fever-reducing (antipyretic) properties. In the
late 1800s, it was found that the natural product salicylic acid was the active ingredient of
this extract that was responsible for these medicinal properties. However, the acidic
properties of salicylic acid, which caused irritation of the membranes lining the stomach
and passages leading to it, prevented its use as a drug. A German chemist, Felix
Hofmann solved this problem by synthesizing the acetyl derivative of salicylic acid,
which had the same medicinal properties of salicylic acid without a large degree of
irritation to mucous membranes. Acetylated salicylic acid (acetylsalicylic acid) was
given the common name aspirin.
In today's experiment, you will acetylate salicylic acid using acetic anhydride
with an acid catalyst, isolated the crude product, and finally purify it by recrystallization.
Precautions
1. Be careful with the concentrated 85 % phosphoric acid, it is corrosive and burns the
skin and eyes.
2. Be careful with the acetic anhydride, it is corrosive and a lachrymator (causes tears).
92
Procedure
1) Weigh salicylic acid (1.0 g) into a 50 mL Erlenmeyer flask.
2) Under a hood, add acetic anhydride (2.0 mL) into the flask and then add five drops of
85 % phosphoric acid. Loosely cork the flask and bring it back to your bench top.
3) Gently mix the contents of the flask for one to two minutes and then let stand for
about 10 minutes. Be careful, the flask will become hot during the mixing.
4) To complete the reaction, loosen the cork and place the flask into a hot (45-50C, hot
tap water in a beaker is sufficient) water bath for about five minutes.
5) With occasional stirring, cool the reaction mixture in an ice-water bath until a large
amount of solid forms.
6) Add approximately 15 mL of ice-water to the reaction mixture and stir the mixture to
break up the crude aspirin.
7) After the ice has melted, filter the reaction mixture and rinse the solid on the funnel
twice with 3 mL of ice-cold water.
8) Purify the crude product by first dissolving it in a minimum amount of ethanol (you
should not use more than 1.5 mL) and then adding 10 mL of hot (55-60C) water into this
solution. Let the solution cool for 10-15 minutes and then cool it with an ice-water bath.
Collect the purified aspirin by filtration.
9) Place the aspirin into a beaker to dry until the next lab period.
10) Weigh the aspirin, transfer it to a sample vial, record the melting point, and hand in
the product to your instructor.
93

NAME_____________________________________
DATE________________
LOCKER #__________
LAB DAY AND TIME_____________________
BALANCED EQUATION:
Name of
Reactant
Grams MM

b Reactant
Produc
Moles
of
Coeff.
t
NAME OF PRODUCT____________________________________
RESULTS
a.
b.
c.
d.
e.

94
Beaker
Boiling chips
xx
Wire Guaze
Ring iron
Bunsen burner
Step 2
Step 1
Ring stand
& clamp
Filter paper
Buchner
funnel
Filter
adapter
to
Trap
Filter
flask
Ice
Water
Step 3
Step 4
Figure 1. Recrystallization technique (diagrammed).
95
Open
Condenser
Water
out
Water
in
Round bottom flask
xx
Heat Source
Figure 2. Reflux Set-up.
96
Boiling chips
Thermometer
Thermometer adaptor
Three-way
connecting tube
Condensor
Vacuum
connecting
tube
Water
out
Distilling flask
xx
Heat Source
Boiling chips
Water
in
Receiving
flask
Beaker of ice/water
cooling flask if necessary
Figure 3. Simple Distillation Set-up.
97
Thermometer
Thermometer adaptor
Three-way
connecting tube
Condenser
Vacuum
connecting
tube
Condenser
Water
out
Water
in
Receiving
flask
Distilling flask
xx
Heat Source
Boiling chips
Figure 4. Unpacked Column Distillation Set-up.
98
Beaker of ice/water
cooling flask if necessary

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TABLE OF CONTENTS

CHEMISTRY 2231 LABORATORY SCHEDULE

GENERAL INFORMATION ................................................................... 4

MELTING POINT ................................................................................ 12

RESOLUTION OF RACEMIC PHENYLSUCCINIC ACID ............................. 23

SYNTHESIS OF TERTIARY BUTYL CHLORIDE......................................... 26

SYNTHESIS OF 2-METHYL-2-BUTENE .................................................. 29

SYNTHESIS OF 2,4,4-TRIMETHYL-2-PENTENE AND ISOMER ................. 32

OXIDATION OF CYCLOHEXENE TO ADIPIC ACID .................................. 35

SYNTHESIS OF 2-METHYL-4-HEPTANONE ........................................... 38

CHECK OUT ....................................................................................... 46

ORGANIC POLYMERS ......................................................................... 47

2241 LABORATORY SCHEDULE

GENERAL INFORMATION ................................................................... 4

COLUMN CHROMATOGRAPHY .......................................................... 52

SYNTHESIS OF 1,4-DI-T-BUTYL-2,5-DIMETHOXYBENZENE ................... 55

THE CANNIZZARO REACTION ............................................................. 58

PART III ............................................................................................. 60

SYNTHESIS OF BENZOPHENONE OXIME ............................................. 67

THE REARRANGEMENT OF BENZIL ..................................................... 70

PREPARATION OF METHYL BENZOATE ............................................... 73

SYNTHESIS OF LIDOCAINE .................................................................. 77

Parts I & II ......................................................................................... 78

Part III ............................................................................................... 79

SYNTHESIS OF DIBENZALACETONE ..................................................... 85

-D-(+)-GLUCOSE PENTAACETATE ...................................................... 88

CHECK OUT ....................................................................................... 91

THE SYNTHESIS OF ASPIRIN ............................................................... 92

NEIGHBORS. ANY QUESTIONS ARE TO BE DIRECTED TO THE

USING THE BALANCES

HEATING IN THE LAB

FILTERING AND DRYING SOLID:

DRYING ORGANIC LIQUIDS (THE REMOVAL OF WATER)

USES OF THE SEPARATORY FUNNEL:

STEP 3: Calculation of the TY based on ethanol:

HOW TO TAKE A MELTING POINT

LITERATURE MELTING POINT, C

LOCKER NUMBER _______

LAB DAY AND TIME ______________

MELTING POINT DATA SHEET

Observed M .P. Range

Results of Mixed Melting Points

Observed M.P. Range

UNKNOWN NUMBER __________

GRADES: Pre-Lab (20):_____ Experimental Technique (30):_____

PART 1: SOLUBILITY TEST FOR THE SOLID TO BE PURIFIED

PART 2: RECRYSTALLIZATION OF AN IMPURE SOLID

It may be necessary to add more solvent to dissolve the crystals ( add in 10 mL

LOCKER NUMBER _______

LAB DAY AND TIME ______________

SOLUBILITY DATA SHEET

Good Recrystal. Solvent (yes/no)

Weight of Crude Solid ______________g

GRADES: Pre-Lab (20):_____ Experimental Technique (30):_____

LOCKER NUMBER _______

LAB DAY AND TIME ______________

DISTILLATION DATA SHEET

UNKNOWN SOLUTION DISTILLATION

RESOLUTION OF RACEMIC PHENYLSUCCINIC ACID

*Stephani, R. and Cesare, V. J. Chem. Educ., 1997, 74, 1226.

NAME________________________________ LOCKER #______________

LAB DAY AND TIME_________________

RESOLUTION OF PHENYLSUCCINIC ACID

GRADES: Pre-Lab (20):_ Experimental Technique (30):_

GRADES: Pre-Lab (20):_ Experimental Technique (30):_

NAME__________________ LOCKER #

GRADES: Pre-Lab (20):_ Experimental Technique (30):_

GRADING: Pre-Lab (20):_ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (30):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_

GRADING: Pre-Lab (20):__ Experimental Technique (30):_