Chem237LabManual-Fall2012 R PDF

CHEMISTRY 237
LAB MANUAL
University of Illinois at Urbana-Champaign

Fall 2012
Prof. Steven C. Zimmerman
TABLE OF CONTENTS
Course Information
Schedule of Experiments and Readings
Procedures and Grading
Penalties for Laboratory Misconduct
Lab Notebook, Lab Reports and Product Sample
Sample Prelab
Lab Report Guidelines
Sample A-1. BAD Lab Report
Sample A-2. GOOD Lab Report
Laboratory Safety
Waste Disposal
Apparatus in Desk
Care of Laboratory Equipment
Protocol for Starting Lab and Laboratory Check-out
How To Illustrations
Obtain a Melting Point Range
Test the pH of a Solution
Use a Separatory Funnel
Perform a Gravity Filtration
Use the Rotary Evaporator
Tare a Flask
Perform TLC Analysis
Set Up a Dean-Stark Trap
Set Up a Simple Distillation
Set Up a Fractional Distillation
Load an IR Spectrum
Take an IR Spectrum
Set Up a Reflux
Perform a Vacuum Filtration
Set Up a Chromatography Column
Select a Solvent for Recrystallization
NMR Sample Submission Instructions
Characteristic IR Stretching Frequencies and NMR shifts
MNovaLite NMR Instructions and Presenting NMR Data in Reports
Experiment 1: Isolation of the Components of BC Powder
Experiment 2: Preparation of Synthetic Banana Oil
Experiment 3: Identification of a Conjugated Diene in Eucalyptus Oil
Experiment 4: NMR (dry lab)
Experiment 5: Acetylation of Ferrocene
Experiment 6: An Unexpected Reaction of 2,3-dimethyl-2,3-butanediol
Experiment 7: Multi-step Synthesis of Fragrances
Experiment 8: Enolate Chemistry Chalcone Derivatives
Page No.
3
6
7
9
10
13
16
18
22
25
35
38
42
43
44-63
63
64
66
68
74
78
81
82
86
88
93
CHEMISTRY 237
COURSE INFORMATION
Instructor:
Prof. Steven C. Zimmerman

Office Location 345 Roger Adams Laboratory
Office Hours Friday 4-5 pm
Email: sczimmer@illinois.edu
TAs:
Badea, Adina
Giovino, Marissa
Kortman, Gregory
Seymour, Craig
Yousaf, Zain
Fall 2012
email: badea2@illinois.edu
email: giovino2@illinois.edu
email: kortman2@illinois.edu
email: cseymou2@illinois.edu
email: zyousaf2@illinois.edu
Lecture:
Mon. 3:00 PM 3:50 PM
Tues. 9:00 AM 9:50 AM
Laboratory:
Section AB1
Section AB2
Section AB3
Section AB4
Section AB5
Tues.
Tues.
Wed.
Thurs.
Thurs.
112 Chemistry Annex

100 Noyes Laboratory
8:00 AM 11:50 AM
1:00 PM 4:50 PM
1:00 PM 4:50 PM
8:00 AM 11:50 AM
1:00 PM 4:50 PM

FOR ANY SECTION CHANGES OR TO DROP

SEE RANDY WILKEY; 250 Noyes Lab; Phone: 244-9350; e-mail: wilkey@illinois.edu
Also, inform WebCT administrators; email: chemwebct@mail.scs.uiuc.edu
HOW TO SUCCEED
BE PREPARED!! Read the experiments in advance and come to lab ready to start.
Familiarize yourself with the background information provided in recommended reading.
WORK EFFICIENTLY!! Plan the optimal use of the laboratory period. ASK
QUESTIONS!! Save yourself from preventable errors and lost time. The teaching
assistants and I are here to help you.
REQUIRED MATERIALS
Lab Manual:
The Chemistry 237 Lab Manual is being made available by email

from the instructor and on the course Compass website.
Text:
Operational Organic Chemistry. Lehman, J.W., 4th Ed., Pearson

Education, Inc., 2009.
Usage Card:
Purchase at Illini Union Bookstore (809 S. Wright Street, Champ.)
Laboratory Goggles: Must be approved goggles. Safety glasses are not acceptable.
Laboratory Coat:
Purchase at IUB, TIS, or Folletts. Aprons are not acceptable.
Lab Notebook:
Chemical Education Resources Notebook (ISBN: 0875402488)

3
RECOMMENDED MATERIALS
Reference:
J.W. Zubrick The Organic Chem Lab Survival Manual 7th Ed.
John Wiley & Sons 2003 (ISBN: 0471215201)
Models:
HGS Researcher Model Set Organic Chemistry B

EXAMS
Exams:
Material on the examinations will be taken primarily from the

lectures, assigned readings, and experiments.
Exam/Quiz Schedule: Exam 1: Oct. 22nd and Exam 2 Dec. 3rd, both in lecture
Quiz 1: Sept. 24th and Quiz 2 Nov. 5th, both in lecture
No make-up or conflict exams
GRADING
The course grade is based on a 820 point scale. The points are earned by performance on
the experiments (~55%) and quizzes/exams (~45%). The breakdown is as follows:
Estimated Course Points: (Subject to change)
Lab Reports ..........................................................400
TA Grade ...............................................................50
Quiz 1 .....................................................................35
Quiz 2 .....................................................................35
Exam 1 .................................................................150
Exam 2 .................................................................150
Total Points for the Course ..................................820
Experiments:
1............................................Isolation of BC Powder
2............................................................... Banana Oil
3........................Conjugated Diene in Eucalyptus Oil
4..........................................................NMR (dry lab)
5..........................................Acetylation of Ferrocene
6....................................... Unexpected Diol Reaction
7................................................ Multi-step Synthesis
8.............................................. Synthesis of Chalcone
............................................................... Total Points:
50
50
50
50
50
50
50
50
400
Criteria for Determination of Final Letter Grades

Historical grade distributions for CHEM 237
Curve and break points
Improvement
TA and instructor evaluations
Academic Integrity
University of Illinois academic integrity policies will be enforced! See the following
website for further information: http://www.uiuc.edu/admin_manual/code/rule_33.html
and the CHEM 237 lab manual for further details.
4
CHEM 237 Fall 2012

*Reading assignments in Operational Organic Chemistry textbook listed with experiments
Week of
Experiment
Aug. 27
LAB: Check In and Begin Experiment 1
(week 1)
DUE: Appropriate Clothing
Sept. 3
(week 2)
LAB: Continue Experiment 1 Note Because of Labor Day, no lecture this week.
DUE: - Pre-lab for Experiment 1
Sept. 10
(week 3)
LAB: Finish Experiment 1 and Begin Experiment 2

DUE: Pre-lab for Experiment 2
Sept. 17
(week 4)

DUE: Pre-lab for Experiment 3; Post-lab for Experiment 1
Sept. 24
(week 5)
LAB: Finish Experiment 3

DUE: Post-lab for Experiment 2
***Quiz 1*** in lecture during the week of Sept. 24th
Oct. 1
(week 6)
LAB: NMR Exercises A and B; work during lab period [Separate Handouts on Website]
Oct. 8
(week 7)
LAB: Begin Experiment 4

Oct. 15
(week 8)

Oct. 22
(week 9)

***Exam 1*** in lecture during the week of Oct. 22nd
Oct. 29
(week 10)

DUE: Pre-lab for Experiment 6; Post lab for Experiment 5
Nov. 5
(week 11)

***Quiz 2*** in lecture during the week of Nov. 5th
Nov. 12
(week 12)

DUE: Pre-lab for Experiment 7; Post-lab for Experiment 6
Nov. 19
(week 13)
Nov. 26
(week 14)
Dec. 3
(week 15)
THANKSGIVING WEEK BREAK

DUE: LAB: CHECK OUT
***Exam 2*** in lecture during the week of Dec. 3rd
General Information: Procedures and Grading

Course Objectives
The aim of Chemistry 237 is to provide you with an opportunity to learn about the
separation, purification, synthesis, and identification of organic compounds, as well as
develop your critical thinking and problem-solving skills. The course consists of weekly
laboratory sections which involve experiments designed to introduce you to a variety of
experimental techniques. You are expected not only to perform the experiments in the
laboratory, but also to understand the principles behind the experiments so that by the end
of the course you will be able to carry out chemical synthesis and to determine the
structure of unknown compounds. Questions at the end of each experiment have been
designed to supplement the concepts learned and encourage critical thinking.
The final experiment will be a culmination of all you have learned during the semester.
You will be given the structure of a compound. Utilizing all of the techniques and
concepts you have learned, you will design the synthesis, purification, and
characterization of the compound. During the final experiment, your TA will evaluate
your performance in the lab and assign you a grade accordingly. Your TA grade will be
based upon demonstration of techniques learned as well as critical thinking and problemsolving skills in the lab.
Laboratory Safety
Read carefully pages 14-30 in the textbook on laboratory safety. It is imperative for your
own personal safety and for the safety of those around you that you be familiar with
prudent practices and laboratory etiquette. In addition to the text, please read the sections
on Safety and Emergency Facilities, Laboratory Safety Guidelines and Waste Disposal in
the syllabus. It is your responsibility to be aware of potential dangers and proper
measures.
The Experiments
Experiments will be performed only in your assigned laboratory section. The schedule for
the semester assumes that you will come to the laboratory each week well prepared and
that you will use your laboratory time efficiently. At some times you will need to work
on two different experiments in one lab period. You must plan ahead. For example, you
should wash the glassware needed for the preparation of isoamyl acetate the week before
you begin that experiment to avoid wasting time waiting for glassware to dry when you
could be carrying out the experiment. TAs have the instructor's authority to send any
students out of lab who are not properly prepared for the lab. Lab time missed for this
reason cannot be made up! In addition, students who are late to lab will be given one
warning and will then lose 5 points for each subsequent late arrival.
The first time a technique is used it will be described in detail. Thereafter it will be
presumed that you can use this technique without further detailed directions. To do this
intelligently, you must acquire not only manipulative skill, but also judgment about what
a given procedure accomplishes and when it should be used. You will be EXPECTED to
become progressively independent of TA assistance as the course advances.
6
Occasionally, "difficulties" arise in the experiments. If the difficulties are judged by the
TA to be of a serious nature and beyond your control, he/she may authorize that you be
given additional starting material and/or extra time. If you are responsible for the
difficulty, a grade penalty (20%) will be assessed for extra starting material. You have
four hours to complete your lab. You will be assessed a penalty of 5% of the grade for
that experiment for every 5 minutes after your allotted time. You will not be allowed to
work in any laboratory period other than your regularly assigned section unless you have
written permission from the instructor and the agreement of the TA supervising your
extra lab.
If you miss a lab period, you must provide the instructor with advance warning or
explanation (school activity, illness, family emergency) to obtain permission to make up
the lab.
Grading
TO GET CREDIT FOR THE COURSE YOU MUST COMPLETE ALL OF THE
EXPERIMENTS.
Each experiment will be graded according to the scheme below. However, the point
distribution will vary according to the characteristics of the experiment, products, and
product data. Reports will be graded on completeness, organization, quality, and
interpretation of physical data and spectra, as well as consistency and clarity of
explanations and conclusions. Graded reports will be returned one week after the due
date.
Academic integrity is essential for scientific credibility! University of Illinois Academic
Integrity Policies will be enforced. Penalties for plagiarism, cheating, falsifying data, etc.
will be assessed by the instructor and according to University policy. Penalties may range
from a zero grade on an individual assignment to a failing grade for the course. See the
following Web site for further information:
http://www.uiuc.edu/admin_manual/code/rule_33.html
Penalties for Laboratory Misconduct in CHEM 237

(Fall Semester 2012)
Misconduct
Penalty
Tardy to lab
Warning (1st time), then 5 pts. off of lab report

per 10 minutes past 1 hour (after 1 hour you
will not be allowed to start experiment)
Unexcused absence
Failing grade for the course
Excused absence (by instructor)
No penalty must make up lab, arrange with

instructor
Late lab report

1-2 days late
2-7 days late
>7 days late
15% of maximum value of lab report;

25% of maximum value of lab report;
not accepted failing grade for the course
Failure to turn in any lab report
Failing grade for the course

Warning (1st time), then 20% of maximum
value of lab report
10% of maximum value of lab report
5% of max value of lab report for every 5
minutes after lab time expires
Additional chemical samples

Duplicate NMR spectrum
Not finishing lab in allotted time
Not wearing goggles or lab coat
10 pts. off of lab report plus expelled from lab

until wearing them; time cannot be made up
Failure to wear proper attire
Sent out of lab until proper attire is worn
Improper waste disposal (including chemicals,

gloves, paper)
Warning (1st time), then 5 pts. off lab report

per offense
Improper dispensing of chemicals

per offense
Failure to close chemical bottles or carboy stopcocks

per offense
Improper glass disposal (including pipettes, vials,

and capillary tubes )

per offense
Failure to turn off and unplug unused equipment
Warning (1sttime), then 5 pts. off lab report per

offense
Negligent chemical spills
10 pts. off lab report per offense
Failure to maintain workspace (chemicals, wet bench

top or floor, trash found),

per offense
Laboratory Notebooks, Lab Reports, and Product

Sample
Notebook
A bound laboratory notebook is required. A suggested one is Laboratory Research
Notebook, published by Stipes. It is critical that all pertinent information be recorded
during the lab period in the notebook. This serves as the primary source of information
for your reports (see below). Read pp. 837-842 in the textbook and see the Guidelines
and Sample Page for Laboratory Notebooks (below) in the syllabus. Leave the first
couple of pages in your notebook for its table of contents.
Prelab
As part of the advance preparation for each experiment, all students must hand in a prelab. The information for the pre-lab is to be recorded in your lab notebook and the yellow
carbon copy sheets are to be handed in at the beginning of the lab period for that
experiment (See attached Guidelines and Sample Prelab in the syllabus).
The pre-lab report must be handed in to your TA before starting material for the
experiment will be issued. You will not be allowed to start the experiment until you have
handed in a satisfactory pre-lab report. If the TA considers your pre-lab report
insufficient, you will be required to fill in any missing information before you are
allowed to continue with the experiment. COME TO LAB PREPARED!!
Lab Reports
The content of the lab report is described in the Guidelines as well as more detailed
instructions at the end of each experiment. Two sample lab reports are also provided. The
reports are to be submitted to the TA on the student's lab day one week after the
completion of the lab. Late reports (up to 2 days) will be assessed a penalty of 15% of the
value of the experiments. Reports turned in between 2 and 7 days late will be assessed
a 25% penalty. No report will be accepted more than one week late.
Postlab Questions
In most cases an extra set of questions covering the reading material and the lab
experiment will be handed out at the beginning of the experiment. Answers to these
questions should be submitted along with the lab report and will be incorporated into the
lab report grade. A thorough record of observations made during the experiment is
essential to answering these questions.
Infrared Spectra
All spectra should be submitted with the reports and be clearly labeled with: student
name, section, spectrum number, experiment number, and compound structure. (See IR
spectroscopy at the end of the syllabus)
NMR Spectra
All spectra should be submitted with the reports and be clearly labeled with: student
name, NMR identification number, section, spectrum number, experiment number, and
compound structure. (See Preparation of NMR samples at the end of the syllabus)
Product Sample:
All compounds made in this course are to be handed in with the lab report. They should
be bottled (liquids require the insertion of a Teflon film liner in the bottle cap; ask your
TA) and labeled with your name, section, contents, tare and weight of contents. Tare is
the weight of the empty vial with the label, cap and liner.
Guidelines for Laboratory Notebooks

Before you begin each experiment, you must write the pre-lab information (also see
more detailed guidelines included with each experiment) in your notebook and show
the carbon copies (yellow sheets) to your TA. The carbon copies must be turned in
with every lab report.
Pre-lab information:
Your pre-lab should contain everything you need to complete the experiment, including
physical constants, procedure, tables to record your data, etc. Although this list is not
exhaustive, you should at least have:
Title of experiment and date;

Balanced equations for any chemical reactions that will occur;
Mechanisms for any chemical reactions (separate from equations);
Table of reagents and products with molecular formulae and molecular weight (see
example of pre-lab)
All pertinent physical properties of solvents (density, boiling, point, etc.)
Literature values for all pertinent physical constants for reagents and products in table
of reagents and products and include source(s) (Handbook of Chemistry and Physics,
Merck Index, etc.);
Calculate the theoretical yield(s);
Summarized procedure (fill in on left side of page only, leaving right side for
observations and procedural changes made during lab period);
Draw tables for recording any data obtained during experiment.
10
During the experiment:

Using short phrases, describe how you proceeded (on right side of page);
Record all observations, paying close attention to: temperature changes, color
changes, evolution of gases, and appearance or dissolution of precipitates;
Note special techniques, apparatus or procedures;
Be sure to record all errors, mishaps or unexpected problems (this will help you
understand the final result of the experiment);
Describe the methods employed for isolation of the products;
Record a crude yield and some description of the material (Note: When recording a
yield, always include the mass or volume and the corresponding percent yield
according to the theoretical yield);
Outline purification procedures. This is best done in table format:
1) crystallization: solvents, amounts, temperatures, melting points, weight, physical
state, and % recovery.
2) distillation: vapor temperature (boiling point), pressure, weight, physical state,
and % recovery.
3) chromatography: column size, adsorbent and amount, eluent, fraction number,
weight, physical state, and % recovery.
4) Record the yield and percent at final stage of purity.
Properly label your infrared and nuclear magnetic resonance spectra sequentially
throughout the semester and keep a record of the labels of each spectrum in both the
notebook and lab report (this way you will not confuse them);
Record any comments that will aid in the interpretation of the outcome of the
experiment or how problems could have been avoided if the experiment were
repeated.
11
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14
Lab Report Guidelines

Name _________________________
Experiment No. __________________
Section ________________________
Date __________________________
Experiment Title
Introduction:
This section states the purpose or the goal of the experiment. In your own words, describe what you believe
this goal to be and briefly state how it was achieved.
Reaction(s)/Table of Reagents:
X + Y
MW:
amount:*
moles:
equiv.:**
misc.:***
Include full structures for the balanced reaction equation. All structures must be drawn using ChemDoodle,
ChemDraw or a similar program, and each student must draw his/her own figures. Molecular formulas
are insufficient. Amounts of reagents in units of mass and/or volume as well as in moles/millimoles are
required.
*amounts can be either mass or volume
**Equivalents are calculated for the starting materials based upon the limiting reagent
***Miscellaneous information includes boiling points, melting points, density, etc.
Theoretical Yield:
Calculate a yield for each step as well as an overall yield (both in moles and grams).
Mechanism:
This section is required if a reaction or series of reactions were carried out. All structures must be drawn
using ChemDoodle, ChemDraw or a similar program, and each student must draw his/her own figures.
Experimental Procedure:
This section contains a detailed yet concise account of how the experiment was carried out as well as any
observations made during the experiment. Use grammatically correct, complete sentences in the past tense.
Passive voice should be used when describing work performed, i.e. the solution was stirred, rather than I
stirred the solution.
Results:
This section is an organized presentation of the data and contains a clear and concise discussion of the
results. All numerical data should be in table format.
Discussion:
Thoroughly discuss the ramifications of any observations and procedural changes, as well as any
implications that can be drawn from the obtained data. Include a brief summarization of the overall results
at the end of the discussion section. This section should be separate from the Results section. It is not
necessary to restate the entire procedure as part of the discussion.
15
Postlab Questions:
The answers to these questions are placed at the end of the lab report. Use grammatically correct, complete
sentences where applicable. Any structures and mechanisms are drawn with ChemDraw. The reader should
be able to understand what the question is asking by reading your answer.
ChemDoodle structure drawing program is FREE for UIUC students thanks to support by the Department
of Chemistry at the University of Illinois. For a copy navigate to:
http://www.chem.illinois.edu/clcwebsite/ChemDoodle.html
16
Sample Lab Report - A-1

(Example of a BAD Lab Report)
Name __________________________
Experiment No. ___________________
Section _________________________
Date ___________________________
Synthesis of n-Butyl Acetate
Introduction:
In this lab Le Chatelier's principal will be used to drive a reaction, and the techniques of
fractional and azeotropic distillation will be learned.
Reactions:
C2H4O2
MW: 60.05
amount: 12.64mL
moles: 0.22
equiv: 1.0
+ C4H10O
C6H12O2
74.12
14.82 g
0.20
1.0
116.6
1.0
MW: 60.05 74.12 116.16 amount: 12.64 mL 14.82 g moles: 0.22 0.20 equiv: 1.0 1.0 1.0
Theoretical yield:
expect to obtain 100% butyl acetate.
Experimental procedure:
First period: Placed .20 mol n-butyl alcohol, .22 mol glacial acetic acid, 3 mL sulfuric
acid, 20 mL hexane, and some boiling chips in a 100 mL round-bottom flask. Then I
filled the side arm of the Dean Stark trap and put it on the round bottom. Placed a reflux
condenser on the Dean Stark trap. Heat the flask until water stops collecting in the trap (3
hours). Then I let the flask cool. Transferred the contents of the flask and the trap to a
separatory funnel, drained off the aqueous layer, and washed the organic layer twice with
two 25 mL portions of water. Dried it with some anhydrous magnesium sulfate.
Second period: Purified the crude liquid by fractional distillation. The fraction distilling
from 120-125 C was nearly pure n-butyl acetate. Took an IR of it.
17
Results and discussion: 20.09 g (.17295 mol) of n-butyl acetate was obtained. This is an
overall yield of 86.47555% from the .20 mol of n-butanol we started with. I would have
gotten more, but I didn't get to let the reaction go the whole three hours (my TA made me
stop after two). Also, the material in my reaction flask turned green (everyone else's
turned pink or purple), so there was probably something wrong with my starting material.
The boiling point of my product is 122.5 C.
IR Data Peak
2973.3
2886.8
Comment
Strength
Hydrocarbon Stretch
Strong
Hydrocarbon Stretch
Strong
Carbonyl derivatives -- cyclobutanone or
Strong
phenol or ester
?
Medium
Esters, Acids, Alcohols (bending)
Medium
Esters in range, 1250-1190 cm-1
Medium
?
Weak
1763.5
1466.3
1373.2
1239.8
1038.5
NMR data
(ppm)
4.10
2.05
1.60
1.45
0.93
Peak Pattern
3
1
Many
Many
1
Integration
2.02
3.11
2.16
1.92
3.09
Assignment
OCH2
CH3CO
OCH2CH2
OCH2CH2CH2
CH2CH3
n-Butyl acetate was prepared in 86.47555% yield by Fischer esterification. The reaction
was driven by making use of Le Chatelier's principle. We used a Dean Stark trap to
remove water as it formed; this kept the back reaction from occurring and thereby drove
the reaction to the right. The Dean Stark trap worked because hexane and water boiled off
as an azeotropic mixture. After they condensed, the water fell to the bottom of the trap
and couldn't get back out. The hexane, being less dense, was able to return to the reaction
flask. The n-butyl acetate was purified by fractional distillation; as the vapor traveled up
the fractionating column, it continually re-condensed and re-vaporized, and this left
impurities behind.
18
Commentary (or why this is a bad report)

Introduction:
1) Use past tense. Future tense was used in the prelab because the lab hadn't been done
yet. Now that it has been done, past tense is appropriate.
2) Don't just give generalities- be specific about the reaction that was done (i.e., butyl
acetate was prepared by Fischer esterification).
Reactions:
1) Give structures. Drawing them by hand is acceptable.
2) The equation must be balanced. Here, one of the products (water) is missing.
3) Report the actual amounts and moles started with, not the amounts listed in the
syllabus.
Theoretical yield:
Report the amount expected in grams and moles.
1) Again, report the actual amounts started with.
2) Report the amounts as they were measured. For instance, the acetic acid was not
measured out in moles- it was measured in grams or milliliters.
3) Use complete sentences.
4) Don't use first person (I, me, my, etc.). For example, "then I filled the side arm" should
be phrased "the side arm was then filled."
5) Keep tenses consistent. Don't alternate between past and present tense.
6) Don't omit crucial details. With what was the side arm filled? Was the magnesium
sulfate removed before fractional distillation? The criterion that should be kept in mind is
reproducibility- can somebody unfamiliar with the lab reproduce what you did from what
you've written?
7) Phrase your sentences unambiguously. For example, washing the organic layer "twice
with two 25 mL portions of water" can be read two ways.
8) Report the temperatures over which material was actually collected, not the ballpark
range from the syllabus. If the range you collected over exactly matches that in the
syllabus, make it clear that you are reporting your actual data. The overall problem with
19
the procedure as written is that it is a restatement of the recipe in the syllabus. It should
instead be a description of what you actually did.
The overall problem with the procedure as written is that it is a restatement of the recipe
in the syllabus. In should instead be a description of what you actually did.
Results and Discussion:
1) Do not start sentences with numbers.
2) Report data in tables- don't bury it in text. This is especially important when more than
one product is obtained (the extraction lab, for instance).
3) Calculate the percentage yield from the amount you started with, not the amount from
the syllabus.
4) Be careful with significant figures. Percentages should be rounded to the nearest whole
number.
5) Reaction times, color changes, and other conditions and observations should be
reported in the procedure section. (Discussion of their ramifications is appropriate for the
results & discussion section.)
6) Boiling (and melting) points should be reported as ranges.
7) In interpreting IR data, don't just copy the listings in the book or handouts. Also, be
sure to report the type of bond that the signal correlates to. IR spectroscopy does not give
functional groups, only a motion of a type of bond.
8) In interpreting the NMR data, use the correct nomenclature for peak pattern
assignments, and peak integration values should be estimated to the nearest integer. Also,
always draw a complete structure above the NMR table to make interpretation and
assignments clearer to the reader.
9) The discussion should include not only how and why the results were obtained, but
what implications can be drawn from the data.
20
Sample Lab Report - A-2

(Example of a Good Lab Report)
Name ___________________________
Experiment No. ____________________
Section __________________________
Date ____________________________
Synthesis of n-Butyl Acetate
Introduction:
n-Butyl acetate was prepared from butanol and acetic acid by Fischer esterification. Azeotropic distillation
was used to remove water from the reaction and drive the equilibrium. The product was purified by
fractional distillation.
Reactions:
MW:
amount:
moles:
equiv.
BP (oC)
Density (g/mL)
60.65
13.1 mL
0.229
1.1
117-118
1.049
74.12
15.19 g.
0.205
1
116-118
0.81
116.16
23.8
0.205
1
124-126
0.88
18.0
3.69
0.205
1
100
1.00
Mechanism:
Glacial acetic acid (13.1 mL, 0.229 mol), n-butanol (15.19 g, 0.205 mol), hexane (21.1 mL), and sulfuric
21
acid (3.0 mL) were combined in a 100-mL round-bottomed flask. A few Teflon boiling chips were added.
The side arm of a Dean Stark trap was filled with hexane, and the trap was fitted onto the flask. A reflux
condenser was attached to the trap. The mixture was heated to reflux for 2 hours, during which time it turned
green. Due to time constraints, the reaction was discontinued before the expected amount of water had
collected in the trap. The mixture was then allowed to cool to room temperature. The contents of the flask
and trap were transferred to a separatory funnel and the green aqueous (lower) phase was removed. The
organic phase was washed twice with 25-mL portions of water and dried over magnesium sulfate. The liquid
was decanted and stored in a 100-mL round-bottomed flask.
Fractional distillation of the organic material was performed one week later. Two fractions were collected;
distillation was discontinued when about 0.5 mL of material remained in the still pot. The first fraction
(12.72 g, bp 58- 72 C) smelled of hexane. The second fraction (20.09g, bp 122- 126 C) had a fruity odor
and was tentatively identified as n-butyl acetate. An FTIR spectrum was taken of the second fraction (neat).
Results:
n-Butyl acetate:
Theoretical Yield
23.81 g.
Actual Yield
20.09 g.
Percentage Yield
84%
Boiling Point
122-126C
IR Data Table
IR data:
Peak (cm-1)
Comment
Bond Type
2973
Strong
sp3 C-H stretch
2886
Strong
sp3 C-H stretch
1763
Strong
C=O stretch
1373
Medium
C-O stretch
1239
Medium
C-O stretch
H-NMR Data Table
NMR data
Chemical
Shift(ppm)
Peak Pattern Integration
Coupling (Hz)
Assignment
4.10
Triplet
2.1
OCH2 (d)
2.05
Singlet
--
CH3CO (e)
1.60
Multiplet
--
OCH2CH2 (c)
1.45
Multiplet
--
OCH2CH2 (b)
0.93
Triplet
2.1
CH2CH3 (a)
22
GC Chromatogram Data Table

compound
RT
Area
% area
% of sample
(by mass)
Sulfuric acid
2.097 2498 3.473
3
Butyl alcohol
2.289 8415 11.701
12
n-Butyl acetate
2.700 61002 84.825
85
(NOTE: PROPERLY LABELED SPECTRA SHOULD ALSO BE APPENDED TO THE LAB REPORT)
Discussion
n-Butyl acetate was obtained in good yield (84 %) by making use of Le Chatelier's principle. Water was
azeotropically removed as it formed and trapped in the Dean Stark apparatus; removal of water prevented
back reaction from occurring, and the equilibrium was thereby driven toward product formation.
The boiling point of the product compares well with the literature value of 124 - 126 C (Handbook of
Chemistry and Physics, CRC Press, 76th Ed, 1995); this indicates that the product was reasonably pure. This
purity resulted from fractional distillation- the fractionating column provided a means for vapor to condense
and revaporize repeatedly, and thereby enhanced separation of mixture components.
Product was lost in two ways. First, time constraints made it necessary to discontinue the reaction before
completion; some of the starting material remained unreacted. Second, a small amount of material had to be
left in the still pot when the fractional distillation was discontinued. This was necessary to prevent the pot
from shattering.
The color change during the reaction probably resulted from action of sulfuric acid on trace impurities; the
effect on yield was minimal.
POSTLAB QUESTIONS:
1) All questions are to be answered in complete sentence form.
2) Any structures and mechanisms should be drawn with appropriate software, not by hand (ChemDraw,
ISIS, etc.)
23
Laboratory Safety
Read the section of the textbook on Safety before coming to your first laboratory session.
You will fill out the Safety-device Location Worksheet during your first laboratory
session.
The importance of safety precautions in a Chemistry laboratory cannot be
overemphasized.
The following safety rules must be followed. Use common sense when working with
chemicals and laboratory apparatus. As safety is an integral part of this course, your TA
will be grading your compliance with these safety rules.
Laboratory Safety Rules
1. You must NOT be in the laboratory without a TA present. The laboratory sessions
are four hours in length. You will not be allowed in lab after your lab session has
ended.
2. Safety goggles for eye protection must be worn properly in the laboratory at all
times. If you need to remove your goggles, step outside the laboratory to do so.
Prescription eyeglasses (even with safety lenses) do not provide adequate eye
protection, especially from the sides. Therefore, you will be removed from the
laboratory if you are found without safety goggles covering your eyes. If wearing
contact lenses, appropriate eye protection must also be worn. It has been determined
that wearing contact lenses in the lab does not present any greater risk than the naked
eye. Contact lenses do not provide any protection from chemical splashing. Therefore,
eye protection must be worn. When use of the eyewash is necessary, contact lenses
must be removed since they prevent adequate and thorough flushing of chemicals from
the eyes. It is advisable to inform co-workers that you wear contact lenses. This will
help insure that proper safety measures can be taken in the event of an emergency.
3. A lab coat must be worn properly at all times while in the laboratory.
4. Closed-toed shoes that completely cover the foot MUST be worn in the laboratory at
all times. Sandals or perforated shoes are not permitted, as broken glass and spilled
chemicals are constant hazards.
5. Shorts and short skirts (above the ankle) will NOT be allowed. Shirts/blouses should
protect the upper body. Loose clothing should not be worn. Do not wear hosiery as it
will melt upon contact with acid and some chemicals.
6. You MUST note the location of the fire extinguishers, safety showers, eyewashes,
and first-aid kits in the laboratory, so that you will know where to obtain these items if
they are needed. You will fill out the Safety-device Location Worksheet during your
first laboratory session.
7. Many of the chemicals used in the laboratory experiments will be new to you. You
should become acquainted with the properties of every new chemical you use. The
Merck Index or CRC Handbook of Chemistry and Physics and www.chemfinder.com
are good sources for finding the properties and toxicities of many organic compounds.
24
Access to material safety data sheets through various web sites can be obtained on the
School of Chemical Sciences Safety Resources Web Page at http://safety.scs.uiuc.edu.
All chemicals should be treated as though they are toxic. Compounds can enter the
body by being absorbed through the skin, or by being inhaled or ingested. Therefore,
(a) Keep vessels covered. Put the caps back on the solvent bottles immediately. Never
evaporate solvents other than water into the atmosphere. Wipe up any spills
immediately. In order to check for odor, hold the sample about a foot away from your
face and gently fan the vapors towards your nose. Do not put anything in your mouth.
(b) You should use the gloves that are available. Keep your hood clean! DO NOT rub
your eyes or your face without first washing your hands. If something does get into
your eyes, remember to wash your eyes with plenty of water and notify your TA. You
should protect your clothing by wearing a lab coat. Always wash your hands
thoroughly before leaving the laboratory session. If you have any cuts or scrapes,
cover them with band-aids, etc., before coming to the laboratory. Never handle door
knobs, elevator buttons, water fountains, etc. with gloved hands as you could
potentially contaminate these items.
(c) To dilute acids, carefully and slowly add the concentrated acid to the water, never
the other way around. This avoids dangerous splattering. Do like you ought to, add
acid to water.
8. Never heat a closed system! Always use boiling chips when heating any liquid, even
water. When heating a test tube, never point it at yourself or at anyone else. Hot
plates/stirrers pose a significant burn hazard. Flammable vapors can ignite when
exposed to hot plates. Keep open solvent containers as far away from the hot plates as
possible, while remaining in the ventilated work station. Keep papers and all
combustibles away from the hot plate. Turn off the hot plate when not in use. Hot plates
and aluminum heating blocks will remain hot for a long period of time after being
turned off. Neither hot plates nor the aluminum heating blocks give any visual
indication that they are hot, so check by holding your hand a couple of inches away
while feeling for heat. Only after checking this way should you attempt to pick up the
aluminum heating block or hot plate. If in doubt, use tongs. Do not wear garments with
loose floppy sleeves or wrist cuffs while heating with the hot plate/aluminum block.
9. Do not use cracked or chipped glassware. Examine your glassware for star
cracks. Broken glassware should be replaced immediately with new glassware
from the storeroom. Do not handle broken glass with your hands. Sweep it up, or
use a piece of toweling to grasp the pieces. The storeroom has leather gloves to
wear while cleaning up broken glassware.
10. No waste products should be discarded down the drain. Properly labeled waste
containers have been provided in the laboratory. If you have any questions as to
where your wastes should go, ask your TA or a storekeeper.
11. In the case of an accident (cuts, burns, reaction to a chemical, etc.), inform your
TA immediately. A limited degree of first-aid is available at the TA desk in the lab.
If you are seriously injured, emergency services will be contacted (9-911) and you
will be taken to the medical center. Report all accidents immediately. Your health
is more important than your grade in Chem 237!
25
12. Never pour chemicals directly from the storage containers directly into your
reaction vessel.
13. Smoking, eating, and drinking are not permitted in the laboratory. Do not bring
food or beverages into the laboratory.
14. No pets are allowed in the laboratory.
15. No horseplay is allowed in the laboratory.
16. No radios, CD players, iPODS or any other electronic device for playing music
can be used while you are in the laboratory. No headphones or ear buds of any sort
are allowed to be worn during lab.
A good perception of your surroundings is very important in a chemical laboratory.
This state of mind requires your full attention. Take care of yourself and your
neighbors. Immediately warn your neighbor if you see him/her doing something
dangerous. It is natural for you to feel somewhat confused at times. Do not hesitate
to ask your TA or the support staff for guidance with the use of the laboratory
equipment or for advice on safety matters. Please respect the fact that other students
must use the common laboratory equipment, such as the balances, melting point
apparatuses, hoods, etc. Take care of this equipment, and clean up your messes
immediately.
26
Safety
The Chemistry 237 laboratory sessions will be held in 263 Noyes Laboratory. This lab
contains the following safety and emergency equipment:
Drench hose/eye wash

used for chemical splash
or debris in the eye.
Eyewash/drench hose is
activated by pulling
paddle lever forward.
27
Eyewash/drench hose can

also be pulled out of
bench to rinse extremities.
When using eyewash,

hold eye open to ensure
proper flushing.
Eyes should be flushed

for a minimum of 15
minutes per eye.
28
Safety showers are

located in each laboratory
bay as well as in the
chemical dispensing area.
Showers are indicated by
a large yellow square on
the floor.
Shower curtains are

provided at shower
locations for privacy
while disrobing.
Curtain should be pulled

around while entering the
safety shower.
29
Safety showers are

activated by pulling the
wall mounted handle out
and down.
Fire extinguishers are

located throughout the
lab.
To use the fire

extinguisher first remove
the seal by twisting and
pulling.
30
Next, pull the safety pin

to remove.
Raise the horn and point

it at the base of the fire
while squeezing the
trigger/handle. Sweep the
base of the fire with the
extinguishing media until
out. Back away to avoid
flash back.
If unsure of your ability

to fight a fire, or if the fire
is too large to safely
extinguish, activate the
fire alarm by pulling the
fire alarm box lever.
The fire alarm is located
in the hallway by the
stairs.
31
Safety
Safety Device Location Worksheet
See Safety Device Location worksheet on next page. You will need to fill this out and
keep it for your reference.
Appropriate clothing
You must wear appropriate clothing in the laboratory at all times. You MUST wear your
safety goggles over your eyes at all times in the laboratory! DO NOT wear loose or
skimpy clothing (saris, neckties, shorts, halter tops, overly large or ragged laboratory
coats). DO wear closed shoes in the lab. DO NOT wear sandals or perforated shoes. Long
hair must be tied back.
For additional laboratory safety information and resources, access the School of
Chemical Sciences Web site page at http://safety.scs.uiuc.edu
Safety-Device Location Worksheet

Chemistry 237
Name: _________________________ Lab Section: ____________ Date: ____________
Before you begin laboratory work in this course, you must be familiar with the location
of the safety devices on the diagram of the lab shown below. Use these symbols:
Quantity
Equipment
Eye-Wash Faucets
Symbol
X
Quantity
Equipment
Symbol
Exits
Overhead Showers
Fire Extinguishers
First-Aid Box
Fire Alarms (in the hallway)
Stairs
Entrance to Chem 237 Lab
Indicate your assigned work area, and then indicate with an *asterisk* the nearest eyewash faucet, overhead shower, fire extinguisher, fire alarm, and two exits. Give the
completed Safety-Device Worksheet to your TA before starting laboratory work.
33
Waste Disposal
All chemical waste must be placed in appropriate containers in the lab. All containers
must be kept closed when not actively adding waste.
All
contaminated
glassware
must be put
in the
containers
located on the
floor throughout the lab.
Glassware
goes in the
white
container.
The white
containers are
for broken
glass or used
scintillation
vials.
34
Pipettes and
capillary
tubes go in
the red
container.
Solid organic
waste should
be put in the
containers
located in the
hood.
35
Organic
liquids should
be placed in
the containers
in the hood.
The label on
the container
indicates the
compounds
that can be
put in it.
There is a
different
container for
each
experiment.
Gloves, paper
towels, filter
paper and
weighing
paper go in
the yellow
containers.
The yellow
containers are
for
chemically
contaminated
non-glass
waste.
36
Apparatus in Desk
Description
Amount
Adapter, distilling #14/20 w/ 10/18
Adapter, vacuum bent #14/20
Beaker, Griffen w/spout 50-mL
Beaker, Griffen w/spout 100- mL
Bottle, polyethylene wash 250-mL
Brush, test tube, small
Clamp, hose spring
37
Picture
Clamp, plastic yellow, #14/20
Condenser, Liebig #14/20
Cork Ring, 100-mL, #2
Cylinder, graduated, 10-mL
Cylinder, graduated, 100-mL
Distillation column #14/20
Filter adapter, neoprene #2
Filter adapter, neoprene #3
Flask, Erlenmeyer, 25-mL
38
Flask, Filter, 50-mL
Flask, round bottom #14/20, 25-mL
Flask, round bottom #14/20, 50-mL
Flask, round bottom #14/20, 100mL
Flask, round bottom #14/20, 250mL
Funnel, Buchner, polyethylene 55

mm
Funnel, powder polyethylene 70

mm
Funnel, powder glass 70 mm/ with

14/20 joint
Funnel separatory Squibb 125-mL

(with stopcock and stopper)
Funnel separatory Squibb 250-mL

(with stopcock and stopper)
Glass Rod, 8"
Policeman, rubber
Rubber bulbs, 2-mL
39
Sodium chloride discs (25x5 mm)

in a jar containing white and blue
dessicant. If the discs are
hazy/chipped, or if the dessicant is
white and purple, see the TA.
Spatulas, steel, 2 blade
Sponge
Stir bar, Fischer brand egg-shape
Stopper, plastic, #14/20
Test tubes 18x150 mm
15
Test tube holder
Tongs, Crucible, 9"
Tube, drying straight Poly 6 in.
Watch Glass
Wax pencil
40
Care of Laboratory Equipment -- General Guidelines

Care of Hot Plates
(1) Always plug the hot plate into a wall outlet.
(2) Never place an empty flask on a hot plate.
(3) The porcelain top of the hot plate should be kept clean.
(4) Never place a container of ether on a hot plate--this is a significant fire hazard.
(5) Remove round-bottom flasks from the heat source immediately after heating is
complete.
Care of Balances
(1) Never weigh directly on the balance pan. Always use the weighing paper provided.
(2) Promptly clean up any chemicals you spill on or around the balance.
(3) Note: The balances weigh to either 0.1 or 0.01 grams.
Care of Melting Point Apparatus
(1) Do not take the temperature above 220 C without the permission of the TA.
(2) Do not break the m.p. capillaries in the apparatus. If a capillary is broken in the
apparatus, please alert the TA.
(3) Make sure the m.p. apparatus is OFF when you are done.
(4) Note: corrections are noted on each thermometer.
Care of Infrared Spectrometers (IR)
(1) Each student should close his/her computer IR window after use.
(2) Do not wear gloves while using IR.
Care of NMR Tubes (NMR)
(1) NMR Tubes are fragile and expensive, treat them accordingly.
(2) Be particularly careful when fixing and removing the cap.
(3) Pour the contents of the NMR tube into the designated disposal container.
(4) Rinse the inside of the tube repeatedly (4 or 5 times) with acetone.
(5) Allow ample time for the tube to dry before preparing your next sample. Be sure that
your sample tube is free of any traces of organic residue and wash solvents (such as
acetone, hexanes, etc.)
Care of NaCl Plates
(1) Clean your plates after every use with acetone.
41
PRIOR TO THE FIRST LAB PERIOD

1. Looking over and printing the Chem 237 syllabus is highly recommended. Or, find your syllabus on the
course Web site. Bring your bound syllabus to lab.
2. Purchase the textbook "Operational Organic Chemistry" (John W. Lehman) at the bookstore.
3. Purchase your Usage Card at the Illini Union Bookstore. This must be turned in no later than the
beginning of the second lab period or you will not be allowed to begin that weeks experiment.
4. Make sure to have safety goggles (not safety glasses), a lab coat, and a bound laboratory notebook (with
carbon copies) for the first lab period. All of these items can be purchased at the Illini Union Bookstore.
5. Read the entire experiment in the syllabus and the designated pages in the textbook.
6. Prepare the prelab according to the instructions in the experiment and guidelines and examples in the
syllabus.
DURING THE FIRST LAB PERIOD
(CHECK-IN/STARTING THE FIRST EXPERIMENT)
1. Go to 263 Noyes Laboratory and obtain your lab drawer assignment, personal information card, and lock
combination card from your TA. Once filled out, return the lock combination card, personal information
card, and usage card (if you have it already) to your TA.
2. Bring equipment to lab: lab notebook, goggles, lab coat, and usage card.
3. Verify the contents of your drawer against the inventory in the syllabus (pg.37-40).
4. Replace any broken or missing items from your TA.
5. Complete the Safety Facilities Test and hand it in to your TA.
6. Hand in your PRELAB to your TA at the beginning of the lab period to obtain the starting materials.
7. During the prelab lecture, you will be shown how to use two important pieces of equipment in the lab:
the balance and the melting point apparatus.
8. Begin experiment 1. By the end of the lab period, you should be able to isolate the three compounds.
42
PROTOCOL FOR CHECKING OUT

(LAST LAB PERIOD)
1. Thoroughly clean all of your glassware and equipment.
2. Lay out the glassware in your hood in the order they appear in the inventory.
3. Check the inventory of your equipment against the master list in the Syllabus.
4. Replace any missing, chipped, cracked, or broken item(s).
5. When the inventory is complete, have a Teaching Assistant check the desk contents. He/She will put the
items back in the desk as they are checked off.
6. Once you leave the lab, you may not return. Be sure you have all of the information you need.
7. Remember to submit your final Lab Report before the deadline!
43
The How To Illustrations

It can be difficult learning to perform a new task, especially when you are completely
unfamiliar with the apparatus involved. In this section, a few illustrations are provided for
various techniques you will use throughout the semester. Feel free to refer to this section
as often as you like, but you should strive for mastery of the technique as soon as
possible, so you can use your time in lab more efficiently.
How to Obtain a Melting Point Range

Place a small amount of the solid on a watch
glass. Obtain a melting point capillary tube
(sealed on one end). Gently tap the open end of
the capillary tube 2-3 times into the solid until a
small amount of the solid is collected in the end
of the tube.
Turn the tube and gently tap the closed end onto
the bench surface until the solid falls down into
the bottom of the tube. Alternatively, drop the
capillary tube (closed end down!) through a
piece of hollow glass tubing placed vertically on
the bench top.
Repeat the steps above as needed to obtain

approximately 1 mm of solid in the bottom of the
capillary tube. Do not load too much sample in
the tube, as it will take longer to melt and cause a
broader melting point range.
44
The melting point apparatus will look similar to

the apparatus on the right. The Mel-Temp is
attached to a digital thermometer which will be
on the bench next to the apparatus. Turning the
black knob clockwise will increase the
temperature, but the numbers on the dial do not
directly correspond to the temperature. The
sample is loaded into the chamber behind the
magnifying lens.
When obtaining a melting point range, be careful
that you do not heat the sample too quickly. The
thermometer does not register temperature
changes instantaneously, so if you are heating
too fast, it will seem that your sample has a
lower melting point than it should. It should take
around 30-60 seconds for a sample to melt
completely.
The best way to accurately determine a melting

point is to prepare two samples: the first one is
run quickly to find the approximate melting
point range; the second one is run more slowly to
get more accurate results. This is much easier
and faster than running one sample very slowly
to avoid overshooting the temperature.
How to Test the pH of a Solution

Obtain a 2-inch strip of pH paper. Make
sure your gloves are clean (even water
will render the pH paper useless). Tear
the pH paper into little pieces and place
them onto a paper towel. Remove a drop
from the solution you are testing with a
pipette and drop onto the paper. Never
dip the paper into the solution! There
are chemicals on the paper which could
contaminate your product. Use the color
guide on the side of the bottle to
determine the pH.
45
How to Use a Separatory Funnel

Set up an iron ring on a ringstand to hold
the separatory funnel. Make sure it is
tightly clamped so the funnel does not fall.
Close the stopcock and place a beaker
under the funnel before adding any liquids.
Always have a container under the funnel,
just in case you forget to close the
stopcock!
Place a stopper in the top of the funnel.

Wrap your index and middle fingers tightly
around the stopper to prevent it from
falling out while you are shaking the
contents. Invert the funnel and shake.
While you are shaking, pressure will build

up inside the funnel, especially if there is a
neutralization occurring (such as with
sodium bicarbonate washes). Make sure to
vent the funnel often to prevent too much
pressure buildup.
With the funnel inverted, open the
stopcock. You may hear a loud hissing as
the gas is released. Continue shaking and
venting until gas is no longer released.
Remember to close the stopcock before
turning the funnel upright. Return the
funnel to the ring as in the first picture.
Remove the stopper before draining the
solution, to prevent a vacuum from forming
in the funnel.
46
How to Perform a Gravity Filtration

Set up a glass funnel as pictured on the right. Obtain a
piece of filter paper (11) and fold it up so that it fits
into the funnel. Wet the paper with the solvent you are
using before you pour the solution through the funnel
(for example, if your solution contains methylene
chloride, you should wet the paper with that).
Pour the solution into the paper, making sure that you
do not fill the funnel too quickly, causing overflow. If
you are filtering a hot solution, place the flask back on
the heat source while you are waiting to keep the
solution hot. If you are going to evaporate the solution
after filtering, you should filter into a tared round
bottom flask (see How to Tare a Flask).
How to Use the Rotary Evaporator

Locate the rotary evaporator closest to
your workstation. There are several
distributed throughout the lab.
DO NOT use the rotary evaporator until there is dry ice in the cold finger. If there is no
dry ice in the cold finger when you need to use it, ask your TA to add some.
47
Attach your flask to the ground glass

joint on the apparatus. Be sure to place a
yellow clamp on the joint to prevent the
flask from falling into the water bath.
The smaller part of the clamp goes
around the top of the joint.
Locate the red power switch just below
the apparatus on the bench. This will
turn on the power to the evaporator and
the vacuum pump below the bench.
Switch on the rotor by flipping the

green switch located on the upper part
of the evaporator. The speed of rotation
is controlled by turning the black knob
clockwise.
To begin evaporation, locate the two
valves on the side of the cold finger
trap. The two way valve (the top valve)
should be pointing toward the vacuum
line, and the pressure release valve (the
bottom valve) should be closed (as
shown on the right).
If the solvent you are evaporating has a

higher boiling point, you may need to
heat the solution. The switch for the
water bath is located on the lower left of
the apparatus.
When you are done with the evaporator,

be sure to open the pressure release
valve, turn off the rotation, and turn off
the main power switch before removing
your sample.
48
How to Tare a Flask

To tare a flask simply means to
preweigh the empty flask. You can
then determine the mass of product by
weighing the flask containing the
product and subtracting the tare value.
First check that the balance is set to
zero by pressing the blue tare button.
If you are going to tare a round bottom
flask, first place a cork ring on the
balance, then zero the balance.
Place the flask on the balance and wait
for the digital readout to stop
fluctuating. Record the mass of the
empty flask in your notebook.
Using a sharpie or permanent marker,

write the mass on the side of the flask.
Be sure to label the flask on the upper
half so the numbers are not smeared
during evaporation. You should also
write some other identifying mark as
well when working with multiple
flasks to prevent confusion.
How to Perform TLC Analysis

Obtain a silica gel plate. Notice that one side is smooth while
the other side is coated with silica. The side coated with silica
is the one you will be using. Be careful when handling the
plate or the silica may flake off. Lightly draw a line with a
pencil 1 cm from the bottom of the plate, being careful not to
scrape the silica surface off. This will serve as your baseline.
Draw evenly spaced dots for the samples you will be testing.
Label them so that you will remember which is which.
49
Place a small amount of each compound you are testing in

separate test tubes and add 5 drops of acetone. Since the best
separations are achieved when this spot is as small as possible,
the solution should be applied with a very small capillary tube.
Place a 4-mm diameter spot of the mixture on each of the three
narrow plates at the pencil mark. Be sure the spots are above
the level of the solvent in the developing tank or they will
dissolve in the solvent and give erroneous results.
Develop the TLC plates in a chamber like the one shown here
using a beaker and aluminum foil. Place a half-circle of filter
paper in the beaker to help increase the vapor pressure and
consequently cause the plate to develop faster. Cover the
bottom of the beaker with your eluent system (refer to
procedure of your experiment). Remove the TLC plate when
the solvent front is within 5 mm of the top of the plate. Mark
the solvent front lightly with a pencil.
Allow the solvent to evaporate and place the plates under a

UV light source (see TA for assistance). If the spots are not
visible under UV light, place the plates in an iodine visualizing
tank. With a pencil, lightly circle the spots on the plate. Make
a drawing of the plate in your lab notebook and be sure to
clearly label the origin and the solvent front as well as the
location of the spots.
You should report Rf values for each compound in each

solvent. Remember that when the mixture contains more than
one compound, each will have its own Rf value. The Rf value is
calculated by measuring the distance traveled by the
compound (x) and dividing by the distance traveled by the
solvent (y) from the baseline.
When you are using TLC to decide upon an eluent system for
column chromatography, you should select the solvent system
that results in the greatest difference in Rf values between the
components in the mixture.
50
y
x
How to Set Up a Dean-Stark Trap

The apparatus for azeotropic distillation is
shown to the right. The Dean-Stark trap is
attached to the round bottom flask and is
topped by a reflux condenser. As with any
distillation, make sure the water hoses are
secured with hose clips and that the ground
glass joints are secured with yellow clamps
(see How to Set Up a Simple Distillation
for further instructions). Make sure water is
flowing through the condenser before you
begin heating.
Water
in
Before you begin, you need to mark the

sidearm of the Dean-Stark trap to let you
know when the distillation is complete.
Check your pre-lab for the calculated
amount of water that will be generated
during the reaction. Add that amount of
hexanes to the sidearm. Mark this level
with a rubber band or permanent marker.
Once you have done this, fill the sidearm
with hexanes and begin heating. Stop when
the water level reaches the mark.
How to Set Up a Simple Distillation
The equipment you will need for a simple distillation is pictured above. In addition, you
will need two water hoses long enough to reach the sink at your workstation. Make sure
the round bottom flasks you use are sufficiently large enough to hold the reaction mixture
or distillate. You should tare any flask that is used for collecting distillate (see How to
Tare a Flask).
51
Ground glass joints should be secured

with yellow clamps to ensure a tight
seal and prevent the apparatus from
falling apart. The smaller half-circle
of the clamp fits around the top part
above the joint.
The thermometer needs to be

positioned correctly to ensure proper
measurement of the temperature of
the vapor. The tip of the thermometer
should be just below the bottom of
the sidearm of the distilling adapter.
This is the point where the vapor will
be condensing and can be considered
to be close to the boiling point of the
liquid.
All hoses must be secured with hose
clips. This is to ensure that the water
pressure does not pop the hose off the
condenser. Press the clip onto the
hose then pinch tightly to fold the
shorter bent hook over the longer end.
A correctly attached hose clip is
shown to the right. Note how the
shorter bent hook is hooked over the
longer end.
52
The completely assembled apparatus

is shown to the right. Notice the
location of the yellow clamps and
hose clips. Make sure water is
flowing in the condenser before you
start heating. Water should flow in
from the right side (or bottom) of the
condenser and flow out through the
left side (or top).
To sink
The flask for collecting the distillate

should be placed in an ice bath, to
help condense the vapors and prevent
the liquid from evaporating.
53
Water in
How to Set Up a Fractional Distillation

The fractional distillation
apparatus is very similar to the
simple distillation apparatus. The
major difference is the addition of
a distillation column between the
stillpot (the round bottom flask on
the aluminum heating block) and
the distilling adapter. This column
allows for greater separation of
liquids with relatively close
boiling points.
Water in
Distilling
column
Once again, check to make sure

your thermometer is positioned
correctly. When distilling liquids
with boiling points greater than
100C, you should wrap the
distilling column and distilling
adapter in aluminum foil, to keep
the glass from cooling and slowing
down the distillation.
54
How to Load an IR Spectrum
Remove sample cap.
Remove and clean (with acetone in the dry well)

the sample holder
55
Place salt plate on sample.
Replace sample cap and take the IR spectrum.
56
How to Take an IR Spectrum

1.
Follow on screen instructions.
2.
Clear away any previous spectra. To do so, click

Views, and clear all spectra. When it asks to save,
click No and clear report.
3.
Click Collect Sample Enter.
4.
If your spectrum is satisfactory, click Analyze

Find Peaks. By clicking above and below the
threshold line, you can include or exclude peaks.
When finished, click OK.
5.
To print click File Print OK (in top right

corner). Click Cancel after page 1 (then OK if an
error window appears).
6.
Collect printout and sample.
How to Set Up a Reflux

A reflux apparatus is pictured on the right.
Be sure to check the procedure for each
experiment to determine whether you
should heat with the aluminum heating
block or with a hot water bath (a hot water
bath can be made simply by filling a large
beaker half full with water and placing on
the hot plate). The still pot is connected to
a condenser, which is in a vertical position
instead of horizontal (as in the simple
distillation apparatus).
To sink
Water in
Once again, ensure that all hoses are

secured with hose clips and water is
flowing through the condenser before you
begin heating. Do not let the vapors escape
through the top of the condenser! If the
vapors climb too high, reduce the heat.
57
How to Perform a Vacuum Filtration

The vacuum filtration apparatus should
never be hooked directly to the vacuum
line at your workstation. It should be
hooked to the vacuum trap provided for
you. The hose from the vacuum flask is
attached to the top of the vacuum trap. The
hose on the side of the vacuum trap is
hooked to the nozzle for the vacuum line.
Be sure to clamp you filtration flask firmly
to prevent it from toppling and spilling
your product. Place the neoprene filter
adapter in the mouth of the flask and insert
the Bchner funnel into it.
To
trap
From
flask
To vacuum
Obtain a piece of filter paper (9) and

place inside the Bchner funnel. Turn on
the vacuum and wet the paper with
whatever solvent you are working with
(for example, if you did a recrystallization
with methanol, you should wet the filter
with cold methanol). Pour the solution
containing your solid onto the filter paper.
Leave the solid under vacuum for several
minutes to remove any remaining solvent.
58
How to Set Up a Chromatography Column

Two types of columns will be
used in this course; either with a
glass frit (pictured on the left) or
without (shown on the right). Be
sure to securely clamp the column
and secure the ringstand to
prevent it from falling over.
Always have a container below
the stopcock just in case the
column leaks. Check the stopcock
to make sure it is assembled
correctly before proceeding (ask
your TA for assistance).
For the columns without a glass

frit, you must first pack cotton
into the tip as shown in the top
picture, and then add a small layer
of sand with an even surface
(pictured on the bottom).
Then for both types of column:
Close the stopcock and add
several mL of your eluent to the
column. Open the stopcock and
allow most of it to drain out.
Close the stopcock.
59
Prepare your stationary phase by

obtaining the recommended
amount of alumina or silica gel in
a large beaker. Add your solvent
system to the solid and stir. You
should add enough solid that the
mixture becomes a slurry, like
quicksand.
NOTE: It can be difficult to
correctly form a slurry with
alumina, as it is heavy and
quickly settles back to the bottom
of the beaker. You will need to
stir rapidly and pour quickly to
get the alumina slurry into the
column. It may take more solvent
to get all of the alumina into the
column.
Once you have formed a slurry,

quickly pour the mixture into the
column and open the stopcock.
Use your glass stirring rod to help
direct the slurry into the column
and prevent bubbles and cracking
later.
If you are working with alumina,
you will need more solvent to
rinse the alumina down the sides
of the column.
60
Once you have a sufficient

amount of your slurry in the
column, pack the stationary phase
by tapping the sides of the column
with a rubber hose. If the solvent
level is too low, add more solvent
until all of the stationary phase
has completely settled in the
column (you should notice when
you first add the slurry that the
level of the stationary phase
slowly drops; the stationary phase
is packed when you no longer see
this occurring).
Allow the solvent level to drop to

just above the top of the
stationary phase and close the
stopcock. Add just enough sand
to create a layer of several inches
on top of the stationary phase.
Drain the solvent to just below the
top of the sand level and close the
stopcock.
Dissolve the crude material in a

small amount of the
recommended solvent (save a
small amount of the crude
material for TLC analysis; refer to
procedure for each experiment).
Using a pipette, add the solution
to the top of the column. Open the
stopcock and allow the solvent to
drain to just below the sand level
and close the stopcock again. Add
the eluent system slowly to the
column, making sure to not
disturb the crude material.
61
Open the stopcock and begin

collecting the fractions. Collect
the eluting solvent as fractions in
separate test tubes. Fill each test
tube approximately of the way
full. Swap to the next test tube as
shown. To determine which test
tubes contain the product,
perform TLC analysis (see How
to Perform TLC Analysis).
How to Select a Solvent for Recrystallization

Place a spatula-tip of the crude solid in a test tube and cover
the solid with a few drops of the solvent you wish to test.
Strike the tube gently to mix and note whether the crude
solid dissolves. If it dissolves, that solvent is not suitable for
recrystallization. If the crude solid does not dissolve, you
can proceed to the next step.
Heat the test tube in a hot water bath until the solvent begins
to boil.
Point the tube away from you and shake it vigorously. Note
whether the crude solid dissolves. If the solid dissolves,
remove from heat and observe whether the solid reforms. If
it does, the solvent is sufficient for recrystallization.
Repeat this procedure with different solvents using small
samples of the crude solid. Be sure to record your
observations in your notebook.
62
NMR Sample Submission

Instructions
Follow instruction sheet in lab.
For liquid samples, dip a micropipette (TLC spotter) into
your sample. Spot the liquid onto the filter.
For solid samples, collect a small amount of sample in the
tip of a Pasteur pipet. Transfer the sample to the filter, and
wipe off any excess material from the sides of the filter.
Place the filter in the sample vial. Using a glass syringe,
draw up 50 microliters (L) of deuterated chloroform
(CDCl3). Carefully inject the solvent into the top of the filter.
This will approximately fill the top of the filter.
Tightly cap the vial. Place the vial in the centrifuge (always
balance the centrifuge!) and spin the vial for 1 minute.
Wait until the centrifuge comes to a complete stop, and
remove the vial from the centrifuge, maintaining the vial in
an upright position.
Unscrew the cap, remove the filter using the filter removal
tool, and replace the cap.
Place the vial in the sample holder in the number
corresponding to your assigned hood number.
To clean the vial: Rinse with CHCl3 (not CDCl3) at the
beginning of the lab period and allow to air-dry in the hood
during the lab period.
63
Spectral Analysis-Infrared Spectroscopy-IR Stretching

Frequencies
Group
O-H, N-H
C-H
(cm2)
Functional Group
Comment
3700-3500
OH(non-hydrogen
bonded)
sharp
3500-3200
OH (hydrogen bonded)
broad
3500-3300
N-H
primary, two bands;

secondary, one band
3200-3000
vinyl or phenyl C-H
3000-2800
alkane C-H
2750
aldehyde C-H
2300-2000
1840-1800
anhydride
1800
acid chloride
1770
cyclobutanone or enol
ester
1740
cyclopentanone
1740-1725
acylic ester
1735-1720
aldehyde
, at 2750
confirms
1725-1700
carboxylic acid
, at 3300-2500
(broad) confirms
1710
acyclic ketone,
cyclohexanone,
1680
confirmatory
bands
usually weak
two bands
phenyl ketone
1690-1640
amide
1690-1640
imine
usually weak
1680-1640
alkene
usually weak
1300-1100
esters in range 1250-1190
64
1560-1540
-NO2
strong
1390-1360
-NO2
strong
970-960
trans alkene
700-650
cis alkene
1000-990
monosubstituted alkene
920-900
monosubstituted alkene
890-860
2,2-distributed alkene
800-700
alkyl chlorides
600-500
alkyl bromides
Common Impurities in NMR Samples:

Impurity
Water
Acetone
Chloroform
Dichloromethane
Ethyl Acetate
n-Hexane
Methanol
Chemical Shift (in CDCl3)

1.56 ppm
2.17 ppm
7.26 ppm
5.30 ppm
2.05 ppm
4.12 ppm
1.26 ppm
0.88 ppm
1.26 ppm
3.49 ppm
Multiplicity
Singlet
Singlet
Singlet
Singlet
Singlet
Quartet
Triplet
Triplet
Multiplet
Singlet
Assignment
H2 O
CH3
CH
CH2
CH3CO
CH2CH3
CH2CH3
CH3
CH2
CH3
Note: For any other common solvents/impurities that may be in your sample, you can
find the information in: J. Org. Chem., Vol. 62, No. 21, 1997, pg 7513.
65
Link to MNovaLite Instructions

To find instructions for using MNova Lite for NMR Data Analysis, please go to:
http://scs.illinois.edu/nmr/handouts/getting_started/MNovaLiteInstruct.pdf
Presenting NMR Data in CHEM 237 Lab Reports

1. Turn in the spectrum properly labeled: Your Name, Section letter, Exp #, Date,
Compound name, and most important compound structure. Also always turn in
a spectrum, which includes all peaks (full) from TMS at 0 ppm to at least
chloroform at 7.26 ppm. Of course if you have peaks beyond chloroform include
them.
2. In results section report the NMR data in a table format with a labeled structure
shown above the table.
NMR Table for n-Butyl Acetate
O
d
e
Shift (, ppm)
4.10
2.05
1.60
1.45
0.93
Peak Pattern
Triplet
singlet
multiplet
multiplet
triplet
Integration
2
3
2
2
3
Assignment
OCH2 d-Hs
CH3CO e-Hs
OCH2CH2 c-Hs
CH2CH3 b-Hs
CH2CH3 a-Hs
Note: The integrations are integers and correspond to the # of Hs in the true structure,
not the integrations from NUTS. The integrations from NUTS may be 3.3 or 2.15,
etcand you cannot have 3.3 Hs. The shifts are reported downfield to upfield (largest
to smallest ). Assignments are done by bolding the appropriate Hs and with a lettering system
as shown above.
3. In your Discussion section, include a section discussing the data obtained from
the NMR and its relevance to the experiment.
4.
In experiments involving identification of unknown compounds, a thorough

discussion of how the structure of the compound was determined from the NMR
needs to be included, discussing chemical shift, integrations, splitting and
coupling.
5. In reaction-based experiments where the structure of the product is known, there

should be a discussion of how the NMR data supports that the desired product
66
was formed not only from indicative peaks found in the product, but also the
absence of peaks that would be found in the starting materials or side products.
For example, for the formation of the ester n-butyl acetate from n-butyl alcohol
and acetic acid:
The CH2 shift of (d) for the product is higher the same shift would be for
n-butyl alcohol, because the electron-withdrawing acetyl group deshields these
protons. This indicates that the ester has formed. Also, the spectrum does not
show any broad singlets that integrate to 1H in either the 2-3 ppm range (which
would indicate an alcohol), or the 10-12 ppm range (which would indicate a
carboxylic acid). Taken together, this evidence indicates that indeed the ester was
formed.
67
Experiment #1: Isolation of the Components of BC Powder

OVERVIEW:
BC Powder, an over the counter pain reliever, contains three components: acetylsalicylic
acid (aspirin), caffeine, and salicylamide:
Each component contains certain functional groups that cause them to be either an acidic,
basic or neutral compound. Most organic compounds, like benzoic acid, are not very
soluble in aqueous solutions. However, if the compound is converted to a salt, like
sodium benzoate, then they become water-soluble:
Benzoic acid is an acidic compound, so the reaction with a base (NaOH) causes the
formation of the conjugate base (benzoate anion). Addition of an acid (HCl) converts the
conjugate base back to the acid. When a mixture of compounds is dissolved in one liquid
(for example, ethyl acetate) and another immiscible liquid is added (like an aqueous
sodium hydroxide solution), the components will be partitioned, or distributed, between
the two solutions based upon their solubility in each. In this case, the benzoic acid would
be converted it to its water-soluble salt and reside mainly in the aqueous solution. Basic
and neutral compounds would not react with the base and would therefore remain in the
organic solution. This way, the components can be separated. This technique is called
extraction, and is a very useful way to isolate components from mixtures. It is sometimes
used to isolate useful components from natural products. Using the technique of
extraction, you will separate the components and by partitioning them between an
organic solution and aqueous solutions of various pH values. Another technique that will
be used is recrystallization. Recrystallization is a purification technique that is used to
separate impurities from a compound based upon differences in solubility. You will use
recrystallization to purify one of the three components and compare its purity to when it
was first isolated by extraction. There are four parts to the experiment, which will be
completed over two weeks.
68
CHALLENGE:
Your challenge in this experiment is to isolate the components of BC powder by
extraction, identify each component and determine the purity by melting point and
TLC analysis; then recrystallize the recovered aspirin and compare its purity to
when it was isolated by extraction.
TECHNIQUES AND CONCEPTS:
You will learn the technique of liquid extraction for the separation of acidic, basic, and
neutral organic compounds on the basis of their solubility in immiscible phases, as well
as the utilization of thin-layer chromatography (TLC), melting point analysis in
determining the purity of a compound, and recrystallization as a purification technique.
The concept of acid-base chemistry with respect to organic functional groups is
introduced.
READ:
Operational Organic Chemistry, pp.585-587 (Cleaning and Drying Glassware,
Using Specialized Glassware), 592-601 (Weighing, Measuring Volume, Making
Transfers), 626-629 (Gravity Filtration), 635-645 (Extraction), 665-673 (Thin-Layer
Chromatography), 680-681 (Drying Liquids), 692-704 (Recrystallization), 737-744
(Melting Point), 834-836 (Laboratory Equipment), 843-847 (Calculations for
Organic Synthesis)
PRELAB:
In your lab notebook, write the following information before coming to lab:
observations and procedural changes made during lab period);
Calculate the expected mass of each component for 2 packages of BC powder;
Literature values for melting point of each component;
Flow chart outlining the experiment, indicating which components were in the
organic and aqueous layers at each point; indicate solutions next to the arrows (see
Operational Organic Chemistry p. 847-848 on how to make a flow diagram and p.
51 for example)
PROCEDURE:
Part 1: Extraction
Accurately weigh the contents of 2 envelopes of BC powder into a tared 100-mL
beaker (See How to Tare a Flask page 49). Add 20 mL ethyl acetate and 10 mL
saturated NaHCO3 solution. Swirl until all of the solids have dissolved (may take a
few minutes). Set up a 125-mL separatory funnel. Make sure the stopcock is closed
and pour in the solution from the beaker. Set out three beakers to collect the extracts.
Insert a stopper in the top of the funnel. (See How to Use a Separatory Funnel page
46). Make sure that the stopper is completely inserted. Keep two fingers over the
stopper as you shake to prevent the stopper from falling out. Be sure to point funnel
away from other people and yourself.
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Invert the funnel and gently shake. Carefully vent by opening the stopcock while the
funnel is inverted to release pressure. Drain aqueous layer into beaker and label it
NaHCO3 extract.
Add another 10 mL saturated NaHCO3 solution to the separatory funnel. Insert
stopper and shake as before while carefully venting. Drain aqueous layer into
NaHCO3 extract beaker with first NaHCO3 extract. Set aside.
Add 10 mL 3M HCl to separatory funnel. Insert stopper and shake as before while
carefully venting. Drain aqueous layer into beaker labeled HCl extract.
Add another 10 mL 3M HCl to separatory funnel. Insert stopper and shake as before
while carefully venting. Drain aqueous layer HCl extract beaker with first HCl
extract.
Drain organic layer into third beaker and label it organic layer.
For each solution, follow the instructions below (See How to Perform a Gravity
Filtration page 47, How to Use the Rotary Evaporator page 47 and How to Tare a
Flask page 49):
Organic Layer Workup:
o To remove any remaining water, add a scoop of anhydrous magnesium sulfate
(enough to cover the end of the spatula) to the beaker labeled organic layer
and swirl. If solution is cloudy, add another scoop (no more than 3-4 scoops
max) and swirl until not cloudy, which indicates residual water has been
absorbed by magnesium sulfate.
o Gravity filter the solution into a tared 100-mL round bottom flask. Place flask
on rotary evaporator and remove ethyl acetate. Weigh flask to obtain weight
of solid. Remove solid from flask and place in a labeled vial.
NaHCO3 Extract Workup:
o Obtain a 2-inch strip of pH paper. Place beaker labeled NaHCO3 extract in
an ice water bath. With swirling, slowly add 6M HCl and check pH
periodically until pH reaches 6, then add an extra 10 mL of 6M HCl to ensure
complete neutralization. A white precipitate should form.
o Stir the solution for several minutes to ensure complete neutralization. Set up
a vacuum filtration flask, topped with a Bchner funnel.
o Attach the hose from the vacuum trap in the hood (do NOT connect directly to
the aspirator!)
o Obtain a circular piece of filter paper and place in the funnel. Wet the paper
with a small amount of cold water, then turn on the aspirator.
o Vacuum filter the solid, washing with cold water to remove any residual
traces of HCl. Allow the solid to dry over vacuum. Once it is dry, transfer
solid to a tared labeled vial.
HCl Extract Workup:
o Obtain a 2-inch strip of pH paper. Place beaker labeled HCl extract into ice
bath. With swirling, slowly add 6M NaOH and check pH periodically until pH
reaches 8, then add an extra 10 mL of 6M NaOH to ensure complete
neutralization.
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o Add 10 mL ethyl acetate to the beaker and swirl to dissolve any solids. Place
solution into separatory funnel. Shake funnel and vent. Drain aqueous layer
back into HCl extract beaker. Drain organic layer into a separate clean
Erlenmeyer flask.
o Place the aqueous solution back into the separatory funnel. Add another 10
mL ethyl acetate. Shake funnel and vent. Drain aqueous layer back into HCl
extract beaker. Drain organic layer into Erlenmeyer flask with organic layer
from previous step.
o To remove water, add a scoop of magnesium sulfate to the organic layer and
swirl. If solution is cloudy, add another scoop and swirl until not cloudy (3-4
scoops).
o Gravity filter the solution into a tared 100-mL round bottom flask. Place flask
on rotary evaporator and remove solvent. Weigh flask to obtain weight of
solid. Remove solid from flask and place in a labeled vial.
Part 2: TLC Analysis (NOTE: See How To Perform TLC Analysis page 49 )
Set up six vials. In the first three, place a small amount of each standard compound
and mark the vials A (acetylsalicylic acid), C (caffeine), and S (salicylamide).
In the last three vials, place a small amount of solid from each extraction step and
mark the vials OL (organic layer), AE (HCl extract), and BE (NaHCO3
extract). Add about 5 drops of acetone to each vial and swirl to dissolve.
Obtain 5 mL of acetone and 5 mL of hexane and mix them together. This will be your
developing solvent (50:50 acetone/hexane). Set up a 100-mL beaker with a half-circle
of filter paper fitted to the inside of the beaker. Rinse the beaker out with 1-2 mL of
the developing solvent, wetting the filter paper. Add enough solvent to the beaker to
just cover the bottom. Cover the top with a watch glass.
Obtain 2 TLC plates and one spotter. On each TLC plate, lightly draw a horizontal
line with a pencil (no pens!) about 1-2 cm from the bottom of the plate. Make 6 marks
(thin vertical lines) evenly spaced along the line. Label each spot underneath with a
pencil (A, C, or S) for the first three marks and (OL, AE, or BE) for the next three.
On the first three marks, carefully spot one of each of the standard compounds (A, C,
or S); then spots one of the extracted compounds (OL, AE, or BE) on the next three
marks. Dont overload the spots; a small spot works best. [You might prepare two
plates, one with light spots and one with heavier spots, to get a feel for the best
amount of material to spot on a TLC plate.] Note: the circles below represent the
sizes of the spots, NOT the markings you should make with the pencil.
Place the TLC plate into the beaker and cover with the watch glass. Allow the solvent
to climb within 1-2 cm of the top of the plate. Take the plate out of the beaker and
71
draw a line where the solvent stopped. Using a UV lamp, circle the spots on the plate
lightly with a pencil. Compare the spots for each of your extracts to the standard
compounds. Calculate the Rf value for each of the three components (acetylsalicylic
acid, caffeine, and salicylamide) and record the values in your lab notebook.
Part 3: Melting Point Range Analysis
Let the all of the solids dry completely before attempting melting point analysis.
Load a small amount of each solid into separate melting point capillary tubes (see
How to Obtain a Melting Point Range page 49). You should prepare two tubes of
each solid, one for a fast run, and another for a slow run.
Obtain the melting point ranges for the three solids and record the results in your
notebook. The starting point of the range is when the sample begins to liquefy and the
final point of the range is when the sample has completely liquefied. Be sure to note
the time it takes for the sample to melt.
Part 4: Recrystallization
Place 1 gram of the isolated aspirin (or all if it if not enough was recovered) into a 50
mL Erlenmeyer flask with a boiling stick.
Put ~20 mL of toluene into another 50 mL Erlenmeyer flask with a boiling stick, and
bring the toluene to a boil.
Carefully add the boiling toluene to the aspirin until just enough has been added to
fully dissolve the aspirin. If there is insoluble material, then heat the flask containing
the aspirin and toluene to a boil until all material dissolves. If not, then just remove
the boiling stick from the solution and set the Erlenmeyer on a cork ring in the hood.
Once the solution has cooled to room temperature, place in an ice bath for 10-15
minutes. If crystals have not formed, either dip a stir rod into the solution and allow
the solvent to evaporate off before dipping it in the solution again, or scratch the
bottom of the flask carefully with a glass stir rod. If crystals still do not form, ask a
TA for assistance.
Collect the crystals by vacuum filtration and measure the mass and melting point of
the recrystallized product.
LAB REPORT:
Follow the Lab Report Guidelines included with this syllabus. Report should include:
Balanced equations for reactions involved during extraction and neutralization
Flow diagram for the extraction procedure, indicating which components were in the
organic and aqueous layers at each point; indicate solutions next to the arrows
Summary table for data including percent recovery and melting point ranges for all
three extracted components
Calculate percent recovery (experimental mass/theoretical mass * 100%) for each
component. Include in summary table and show calculations.
Include drawings of TLC plates, tabulate Rf values for all three components
For the discussion portion:
Discuss what the results of the extraction indicate about each component; for each
extraction, is the aqueous solution: strongly acidic, strongly basic or weakly basic?
What does that indicate about the compound that dissolves in that solution?
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Discuss the percent recovery for each component and how it could have been affected
(i.e. spillage, insufficient neutralization, etc.)
Discuss your results from melting point and TLC analysis and what they indicate
about the purity of each component
Discuss the results of comparing the melting point of recrystallized aspirin to the
melting point of the aspirin after isolating it from extraction, and compare
recrystallization and extraction as purification techniques.
QUESTIONS:
A handout will be given to you containing the postlab questions for this experiment.
Use complete sentences to answer the questions. Any structures and mechanisms
should be drawn with appropriate software, not hand-drawn. The assigned readings
are usually an excellent place to being searching for answers.
Make sure that your answers to the postlab questions are included at the end of your
postlab report.
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Experiment #2: Preparation of Synthetic Banana Oil

OVERVIEW:
Many of the flavors and perfumes we use today are derived from compounds found in
nature. Usually, these compounds are separated from natural sources by a variety of
techniques, like extraction or distillation. Sometimes, however, there may be only a
limited supply of the natural source, or the process required to isolate a certain
component is simply too difficult or expensive to be commercially viable. In these cases,
scientists will often find a method to cheaply and efficiently prepare the component
synthetically. In this experiment you will prepare isoamyl acetate, which is commercially
sold as synthetic banana oil. Isoamyl acetate is synthesized by heating isoamyl alcohol,
glacial acetic acid, and sulfuric acid (catalyst) in hexane, followed by fractional
distillation to acquire the desired product. The esterification is a reversible reaction and
exists in equilibrium, as illustrated below:
Removing one of the components during the reaction can shift the equilibrium position.
In this case, by removing water from the reaction mixture, the equilibrium will be shifted
to the right, and more of the products will be formed. This will increase the efficiency of
the reaction. One method to remove water from a reaction mixture is azeotropic
distillation. When two liquids form an azeotrope, the boiling point of the mixture is
related to the relative concentration of the components. There are two types of
azeotropes: maximum-boiling and minimum-boiling azeotropes. In this experiment,
hexane forms a minimum-boiling azeotrope with water. A Dean-Stark trap allows for the
separation of water from the refluxing mixture. As the vapor (containing a mixture of
water and hexane) condenses, the denser water becomes trapped in the sidearm while the
lighter hexane flows back into the reaction flask. This way the water is continuously
removed from the reaction.
CHALLENGE:
Your challenge in this experiment is to synthesize isoamyl acetate and purify it by
fractional distillation. You will also characterize the product by IR spectroscopy and
assess its purity by gas chromatography.
You will learn the technique of gas chromatography as a method of qualitative and
quantitative analysis, as well as the technique of NMR spectroscopy to characterize a
compound and assess the products purity. Concepts introduced include esterification,
azeotropes, LeChateliers principle and driven equilibrium.
74
READ:
Operational Organic Chemistry, pp.70-77 (Preparation of Synthetic Banana Oil;
note procedural changes!), 621-622 (Water Separation), 758-769 (Gas
Chromatography), 802-815 (Nuclear Magnetic Resonance Spectroscopy)
Also review: pp. 606-608 (Hot Plates and Heating Blocks), 609 (Smooth Boiling
Devices), 678-682 (Washing Liquids and Drying Liquids), 710-719 (Simple
Distillation), 727-736 (Fractional Distillation) 744-746 (Boiling Point), 773-792
(Infrared Spectroscopy; also refer to pp.793-801 for Characteristic Infrared Bands)
PRELAB:
Balanced equation for esterification reaction;
Mechanism for the esterification (separate from balanced equation);
Table of reagents containing all starting materials and products, with data filled in for
all pertinent physical properties (MW, bp/mp, density, concentration, etc.);
Density and boiling point of solvents (hexane)
Theoretical yield for products (water too!);
observations and procedure changes made during lab);
Calculate the volume of water that will be formed during the reaction (you will use
this to monitor the progress of the reaction).
PROCEDURE:
Into a 50-mL round bottom flask, place 7.5 mL of isoamyl alcohol, 4.0 mL of glacial
acetic acid (17.4M), 1 mL of concentrated sulfuric acid, and 7 mL hexane along with
2 or 3 boiling chips. (To get an accurate mass of isoamyl alcohol it is recommended
to weigh the vial and sample before, and once added clean the vial, allow to dry and
get weigh again. The difference is the starting material mass).
Obtain a Dean-Stark trap (See How to Set Up a Dean-Stark Trap page 51). Refer to
your prelab and find the volume of water that should be generated during the reaction.
In a graduated cylinder, measure out hexane to that volume. Add the hexane from the
graduated cylinder into the Dean-Stark trap. Use a marker to mark where the top of
the solvent line is. This mark will help you determine when to stop the reaction. Fill
the trap to the joint with hexane.
Connect the trap with the flask and condenser. Make sure water is flowing through
the condenser before you begin. Heat using a hot plate aluminum block until the
mixture begins to reflux vigorously (hot plate setting should be close to maximum in
the beginning until refluxing becomes vigorous, then heat should be slowly turned
down to get a steady, vigorous reflux). DO NOT allow vapor to escape the top of the
condenser! Wrap the tube in between the flask and the condenser, and the top of the
flask in aluminum foil to ensure that heat is contained within those areas. Reflux
until the water level in the trap reaches the mark you made (0.5 to 1.5 hours).
Discontinue heating and allow reaction flask to cool completely to room temperature.
75
Transfer contents of the reaction flask and trap into a 125-mL separatory funnel.
Remove the aqueous layer. Wash the organic layer twice with 10 mL portions of
water and set the aqueous washes aside.
Add ~10 mL of 5% NaHCO3 solution to the organic layer in the separatory funnel.
Continuously swirl the contents with the top of the funnel open until fizzing
decreases. Stopper the funnel and gently shake, venting often to release any pressure
generated by CO2 gas. Remove the aqueous layer and set aside.
Wash the organic layer with ~10 mL brine (saturated NaCl solution). Allow the two
layers to set in the funnel for several minutes before separating. The organic layer
should become not cloudy.
Transfer the organic layer to a clean dry flask and add anhydrous magnesium sulfate
with swirling until solution is no longer cloudy. Gravity filter the organic layer into a
clean, dry 25-mL round bottom flask equipped with 2-3 boiling chips. Tightly stopper
the flask and wrap stopper in parafilm. Return Dean-Stark trap before leaving lab!
Set up a fractional distillation apparatus, with the flask containing your crude product
as the stillpot. Make sure you place the thermometer correctly. Collect fractions as
indicated by temperature changes at the top of the column. The fraction distilling
above 135C should be nearly pure isoamyl acetate. You may have to wrap the
apparatus in aluminum foil to maintain higher temperatures.
Collect the final fraction in a tared round bottom flask. Record the boiling point range
for the product and determine the weight and yield.
Save a small sample for IR analysis and prepare an NMR sample of the product and
submit it for analysis.
NOTE: Once you have been notified that your NMR has been run, you are
responsible for downloading the FID file as soon as possible and checking that
there are no issues with the file. You must inform a TA immediately if there is an
issue so the TA can help to resolve it in a timely manner. If you wait until the day
before the report is due and a problem occurs, the TAs will not be able to help you
and you will still have to turn in your lab report on time.
LAB REPORT:
Balanced equation for esterification reaction
Mechanism of esterification reaction (It is advisable to look up esterification in your
Chemistry 236 text)
Calculate percent yield (experimental yield/theoretical yield * 100%)
Summary table with experimental yield, percent yield and boiling point range for
product
Summary table for IR spectrum data (include original printout with report)
Summary table for GC chromatogram data (include original printout with report)
Discuss LeChateliers principle and why a Dean-Stark trap is used
Discuss percent yield of product and and how it could have been affected (i.e.
reaction time, insufficient distillation, etc.)
76
Fully interpret the data on the IR spectrum.

Discuss the purity of your product based on bp, IR, and GC analysis
QUESTIONS:
Make sure that your answers to the postlab questions are included at the end of
your postlab report.
77
Experiment #3: Identification of a Conjugated Diene in Eucalyptus Oil

OVERVIEW:
Eucalyptus oil is a common homeopathic remedy that is often used in respiratory
illnesses. The most widely used variety is extracted from the species Eucalyptus globulus,
and is composed mainly of eucalyptol:
Eucalyptol may cause inflammatory reactions in some people, however. Another species
of eucalyptus, Eucalyptus dives, which does not contain eucalyptol, has been indicated to
be a more hypoallergenic option and can be used in topical applications. One of its
components is believed to have other potential pharmaceutical applications, such as in the
treatment of colds, malaria and fevers. It is thought to be one of the conjugated dienes
below:
The isolation of natural products is a very important way to discover new drugs with
interesting pharmaceutical properties. Researchers use a variety of methods to isolate
components from natural sources, such as extraction or distillation. These methods are
not efficient, however, when many of the components in the mixture have very similar
properties. Another method to separate components is to form a derivative of the desired
component by selectively reacting it with a specific reagent. The resulting product will
then have different properties that will allow for separation of the product from the
reaction mixture. In this experiment, you will isolate and identify the conjugated diene in
the oil by forming a derivative of the component so that it will form a solid and
precipitate from the solution. You will use the Diels-Alder reaction, in which a
conjugated diene reacts with a dienophile (in this case maleic anhydride):
The Diels-Alder reaction is a highly efficient method to form carbon-carbon bonds. Since
the product contains all of the atoms from the starting materials, the reaction is
considered to have 100% atom economy. Atom economy has become highly desirable in
green chemistry, to reduce the amount of waste produced during industrial processes. The
Diels-Alder reaction is also stereoselective, as usually only one stereoisomer is likely to
form out of several different possible stereoisomers (see textbook for more in-depth
explanation).
78
In order to determine how much of the reagent is needed, you will use GC analysis to
calculate the fraction of the active component in the oil based upon the area of the peaks.
The TA will provide you with a correction factor based upon a standard calibration of the
instrument. Once the solid has been isolated, you will purify the compound by
recrystallization and determine the identity of the derivative by obtaining its melting
point range and interpreting the NMR spectrum.
CHALLENGE:
Your challenge in this experiment is to isolate and identify a component in
Eucalyptus dives oil by performing a Diels-Alder reaction to form a solid and purify
it by recrystallization.
This experiment illustrates the concept of changing a physical property by formation of a
derivative to isolate a component from a mixture. Utilization of a melting point and NMR
spectroscopy to identify an unknown compound is also illustrated.
READ:
Operational Organic Chemistry, pp. 271-277 (Identification of a Conjugated Diene
from Eucalyptus Oil; note procedural changes!)
Also: Review Basic Operations from previous experiments; (Gas Chromatography),
773-792 (Infrared Spectroscopy; also refer to pp.793-801 for Characteristic Infrared
Bands), 609-613 (Heating Under Reflux), 629-633 (Vacuum Filtration), 685-687
(Washing and Drying Solids), 692-700 (Recrystallization), 802-811 (NMR
Spectroscopy)
PRELAB:
Balanced equation for the Diels-Alder reaction (use molecular formula for product);
Structures of all potential products with -myrcene, allo-ocimene, -phellandrene,
and-terpinene;
Table of reagents containing starting materials (include all potential dienes from
above) and potential products (there are 5), with the data for all pertinent physical
properties (MW, bp/mp, density, concentration, etc.). Data other than MW and MP
are not necessary for potential products. You may refer to the products as -myrcene
adduct, allo-ocimene adduct, etc.;
observations and procedural changes made during lab period).
PROCEDURE:
***NOTE: All glassware must be dry for the reflux portion of this experiment***
You will receive a GC chromatogram of the Eucalyptus dives oil (via compass).
Examine the chromatogram and determine the relative concentration of the peak
corresponding to the diene (the percent area is roughly equivalent to the percent
mass). Then calculate the amount of maleic anhydride needed for the reaction.
79
In a 25-mL round-bottom flask, dissolve 5.0 grams of Eucalyptus dives oil in 10 mL

of petroleum ether. Add calculated amount of maleic anhydride and top the flask with
a reflux condenser. Be sure water is flowing in your condenser before you begin
heating. Reflux the reaction mixture for approximately 45-60 minutes.
Transfer the warm reaction mixture to a small beaker. Cover with a watch glass and
let it cool slowly to room temperature. If no crystals form after cooling completely,
dip a stirring rod in the solution and pull it out. Let the ether evaporate from the rod
and reinsert it in the solution. If that doesnt work, scratch the side of the flask with
the tip of the rod. If neither method works, ask the TA.
Once crystallization seems complete, cool the flask in an ice-water bath for 5
minutes. Collect the crystals by vacuum filtration. Wash the crystals with 10 mL of
cold petroleum ether.
Weigh the crude product before performing mixed-solvent recrystallization using
acetone and water to purify it. Dissolve the crude product in minimal acetone. Add
water to the solution. You should see crystals form immediately. Continue to add
water until no new crystallization is observed. Vacuum filter the crystals, wash with
cold water, and dry with suction. Then weigh the pure product, measure its melting
point, and acquire and IR spectrum.
LAB REPORT:
Balanced equation for the Diels-Alder reaction (show stereochemistry of product)
Mechanism of the Diels-Alder reaction (this is separate from the balanced equation!)
Calculate percent yield (experimental yield/theoretical yield * 100%)
Summary table with experimental yield, percent yield and mp for product
Summary table for IR spectrum data (include original printout with report)
Summary table for GC chromatogram data (include original printout with report)
Calculate the relative amount of starting diene based on experimental yield of product
and compare this to the relative amount of starting diene as determined by GC
analysis
Discuss how you decided upon the identity of the diene
Discuss percent yield of product and and how it could have been affected by reaction
conditions (i.e. reaction time, temperature of reflux, etc.)
Discuss the purity of your product based on mp and IR
QUESTIONS:
80
Experiment #4: NMR exercises

Pre-lab and lab exercises are on compass.
81
Experiment #5: Acetylation of Ferrocene

OVERVIEW:
Benzene, which is a common component of petroleum, is often converted to other useful
compounds by various methods of functionalization. One method often performed at
industrial scale is the Friedel-Crafts acylation, which adds a ketone functionality to the
ring. These ketones can then be further convertered into other useful compounds. The
Friedel-Crafts acylation of benzene is a type of electrophilic aromatic substitution
reaction. The major drawback is that it usually requires aluminium chloride, which is
toxic, as the catalyst. Problems such as this have driven many industries to search for
cleaner, greener methods. Some compounds are more susceptible to electrophilic
aromatic substitution reactions and can be acetylated under milder, less toxic conditions.
Ferrocene, Fe(C5H5)2, is an organometallic compound with an Fe2+ cation coordinated
between two C5H5- anions:
Ferrocene has properties similar to benzene in that the cyclopentadiene anion rings have
six delocalized pi electrons. Ferrocene, however, can be acetylated under milder
conditions with phosphoric acid as the catalyst. The Friedel-Crafts acylation of ferrocene
is shown below:
The acylium ion, CH3CO+, is the electrophile that is generated from acetic anhydride. It
reacts with ferrocene to yield either 1-acetylferrocene or 1,1'-diacetylferrocene. Since the
acyl group is a deactivating group, the second substitution is less likely to occur and so
very little of the disubstituted product is formed. In this experiment, you will perform the
acetylation of ferrocene and separate the product from the reaction mixture by liquid
column chromatography. Ferrocene and its derivatives are very brightly colored
compounds, so you will easily be able to visually monitor the progress of the separation
of the components on the column.
82
CHALLENGE:
Your challenge in this experiment is to perform the Friedel-Crafts acylation of
ferrocene, isolate the desired product by liquid column chromatography, and
identify the products by IR and NMR spectroscopy and melting points.
The main technique introduced in this experiment is liquid column chromatography. TLC
will be used to distinguish which bands on the column correspond to starting materials
and products. Also illustrated is the concept of Friedel-Crafts acylation.
READ:
Operational Organic Chemistry, pp. 306-308 (Friedel-Crafts reaction theory), 609613 (Heating Under Reflux),656-664 (Liquid-Solid Column Chromatography)
Also: Review Basic Operations from previous experiments, specifically 629-633
(Vacuum Filtration), 665-673 (Thin-Layer Chromatography), 737-744 (Melting
Point) 773-792 (Infrared Spectroscopy; also refer to pp.793-801 for Characteristic
Infrared Bands)
PRELAB:
Balanced equation for the Friedel-Crafts acylation;
Mechanism for the Freidel-Crafts acylation (separate from equation);
Theoretical yield for all potential products;
Table of reagents containing all starting materials and possible products, with the data
for all pertinent physical properties (MW, bp/mp, density, etc.);
PROCEDURE:
Part 1: Synthesis and TLC analysis
Accurately weigh 0.5 g of ferrocene and transfer to a dry 25-mL round bottom flask.
Add 5.0 mL of acetic anhydride and swirl. Then slowly add 1.0 mL of 85%
phosphoric acid and swirl the mixture.
Attach a reflux condenser (see How to Perform a Reflux page 56) and heat the
reaction to reflux on the aluminum blocks for 1 hour (start timing from when the
solvent condenses on the reflux condenser). After 1 hour, remove the heat source and
allow solution to cool to room temperature (about 10 minutes).
Pour the solution onto approximately 40 g of ice in a large beaker. Neutralize the
solution by dropwise addition of 6M NaOH, checking the pH periodically until the
solution is neutral, then add an extra 10 mL of 6M NaOH.
Cool the solution in an ice-water bath and collect the crude product by vacuum
filtration. Remove as much water as possible by allowing the solid to remain under
vacuum filtration for another 15 minutes. Obtain the weight of the crude product.
While the solid is drying, prepare a TLC plate with two lanes. Dissolve a small
amount of ferrocene in toluene (1-2 drops) and spot the first lane. Dissolve a small
amount of the crude solid in a few drops of toluene and spot in the second lane.
83
Mix 5 mL of hexane and 5 mL of ethyl acetate (1:1 hexane/ethyl acetate) for eluent.
Prepare TLC chamber and develop TLC plate. Record results in your notebook,
including a sketch of TLC plate.
Part 2: Column chromatography and TLC analysis

Obtain a chromatography column and securely clamp it in a vertical position (see
How to Set Up a Chromatography Column page 58). Pack a small amount of
cotton into the tip of the column and add a small layer of sand over the cotton to
provide a level surface for the stationary phase.
Prepare first eluent by mixing 90 mL of hexane and 10 mL of ethyl acetate (9:1
hexane/ethyl acetate). Close the stopcock and add several mL of eluent to the
column. Drain a small amount of eluent from the column then close the stopcock,
leaving a small layer of liquid in the bottom of the column.
To prepare the stationary phase, obtain about 18 g of silica in a small beaker. With
stirring, add enough of the 9:1 hexane/ethyl acetate eluent to cover the silica. Stir
until the silica forms a slurry (add more eluent if necessary). Pour the slurry into the
column in a steady stream (silica settles quickly, so slurry must be poured as quickly
as possible). Open the stopcock and allow the solvent to drain to just above the top of
the silica.
While draining, tap the side of the column continuously with a piece of tubing so that
the silica settles evenly and uniformly. Once the solvent has reached just above the
silica, close the stopcock.
Add a small layer of sand to the top of the column. Drain the eluent until the level is
just below the sand, but not below the top of the silica.
Dissolve the crude product in a minimal amount of toluene (no more than 1.5 mL;
there may be some insoluble residue, just ignore this). Pipette the toluene solution on
top of the sand layer. Rinse the container with another 1 mL of toluene and add this to
the column. Drain the solvent level until it is again just below the sand layer, but
above the silica layer.
Carefully fill the column with 9:1 hexane/ethyl acetate eluent without disturbing the
sand layer. Open the stopcock and collect the solvent in a test tube to a level that you
decide. Continue collecting the portions in test tubes to approximately this level. A
bright yellow band will move down the column. As the solvent level becomes low in
the column, add more eluent until the yellow band is completely off the column and
the first orange band is either off the column or near the bottom of the stationary
phase.
In order to elute the next bands, the eluent system must be changed. For the second
eluent, combine 50 mL of hexane and 50 mL ethyl acetate (1:1 hexane/ethyl acetate).
Allow the solvent to drain to just below the sand layer and close the stopcock.
Carefully add the 1:1 hexane/ethyl acetate eluent and re-open the stopcock.
Continue collecting the portions in test tubes, adding solvent to the column as needed.
Perform TLC analysis on each portion to determine what compounds are in each
portion. Place the solutions for each pure compound (one spot in each lane) in a tared
round bottom flask and remove the solvent. Let the solids dry until next week.
84
Obtain the mass and melting point rangefor each component obtained from the
column purification. Using the melting point, determine which band corresponds to 1acetylferrocene, acquire an IR spectrum, and submit a sample for NMR. Submit the
product(s) in labeled vials.
LAB REPORT:
Balanced equation for formation of acetylferrocene and diacetylferrocene
Mechanism of Friedel-Crafts acylation only mechanism for formation of
acetylferrocene is necessary, not diacetylferrocene.
Calculate percent yield (experimental yield/theoretical yield * 100%) for all products
Summary table with experimental yield, percent yield and mp for all products
Summary table for IR and NMR spectral data (include original printouts with report)
Fully interpret the data on the IR and NMR spectra; compare the spectra of the
products to the spectra of ferrocene, point out and explain any significant similarities
or differences
Include a drawing of your TLC plates, labeling the spots and calculate the Rf values
Explain in detail how you determined the which band corresponded to which
component
Discuss the effectiveness of your reaction based on the yield.
Based on spectral analysis and mp, comment on the purity of your products
QUESTIONS:
85
Experiment #6: An Unexpected Reaction of 2,3-dimethyl-2,3-butanediol

OVERVIEW:
You are working as a synthetic chemist for a company and have been asked to investigate
an efficient method to produce the compound 2,3-dimethyl-1,3-butadiene. You decide to
do the classic acid-catalyzed dehydration of 2,3-dimethyl-2,3-butanediol to obtain the
conjugated diene. You know that the diene has a boiling point of about 70C. To your
surprise and disappointment, you obtain a liquid with the molecular formula C6H12O:
HO
OH
H2SO4
C6H12O
2H2O
Researchers often encounter the problem of reactions not proceeding as they should, even
when using methods that are usually straightforward. In order to determine whether a
reaction has proceeded as desired, the product has to be qualitatively analyzed. There are
a variety of methods used to obtain the structural information of a compound. You will
utilize one of these methods, infrared (IR) spectroscopy. You will perform the acidcatalyzed reaction with 2,3-dimethyl-2,3-butanediol and determine the identity of the
unexpected product by IR and boiling point. You will purify the product by fractional
distillation.
CHALLENGE:
Your challenge in this experiment is to determine what is actually happening during
the reaction by isolating the unknown product and determining its structure by IR
and boiling point.
You will learn the technique IR analysis as a method to determine the structure of an
unknown compound. You will also utilize the technique of distillation for the purification
of liquids.
READ:
Operational Organic Chemistry, pp. 265-270 (An Unexpected Reaction of 2,3Dimethyl-2,3-butanediol; note procedural changes!), 606-608 (Hot Plates and
Heating Blocks), 609 (Smooth Boiling Devices), 678-682 (Washing Liquids and
Drying Liquids),710-719 (Simple Distillation), 727-736 (Fractional Distillation), 773792 (Infrared Spectroscopy; also refer to pp.793-801 for Characteristic Infrared
Bands)
PRELAB:
Balanced equation for the reaction (use molecular formula for product);
Theoretical yield for the potential product;
Table of reagents containing all starting materials and potential products, with the
data for all pertinent physical properties (MW, bp/mp, density, etc.);
observations and procedure changes made during lab).
86
PROCEDURE: (You must monitor/record your boiling points carefully!)

Weigh out 3.6 grams of 2,3-dimethyl-2,3-butanediol (2,3-dimethyl-2,3-butanediol)
and transfer to a 25-mL round bottom flask. Add 10 mL of 3M sulfuric acid and a
magnetic stir bar to the flask.
Set up a simple distillation apparatus (see How to Set Up a Simple Distillation page
57) with a 25-mL round bottom flask as the receiving flask. Be sure to place the
receiving flask in an ice-water bath. Using a heating block, heat the solution until you
have filled the receiving flask about half full (temperature should be over 100C).
Transfer the distillate to a separatory funnel. Rinse the round bottom flask with a few
mL of distilled water and add this to the separatory funnel. Separate the organic layer
from the aqueous layer.
Place the organic layer back in the funnel. Add 6 mL of saturated sodium chloride to
the funnel. Swirl the solution, then stopper the funnel and shake. Place the funnel
back on the stand and remove the stopper. Let stand for several minutes. Separate the
organic layer from the aqueous layer.
Transfer the organic layer to a clean, dry Erlenmeyer flask. Add magnesium sulfate
with swirling to dry the solution (until no longer cloudy). Filter the solution into a
clean, dry round bottom flask.
Purify the product by fractional distillation (use clean, dry glassware! See How to Set
Up a Fractional Distillation page 54). In order to do this efficiently, add 2 mL DMF
to the flask containing the product to be purified. There could possibly be two
fractions: 70-75C and the unknown. Be sure to record the boiling point range of
each fraction. Collect the fractions in preweighed, clean, dry flasks (not a vial!
Product is very volatile).
Obtain an IR for each fraction that is obtained (see How to Obtain an IR Spectrum
page 54).
LAB REPORT:
Balanced equation for formation of unexpected product
Mechanism of formation of unexpected product
Balanced equation for formation of diene
Mechanism of formation of diene
Summary table with experimental yield, percent yield and bp for all products
Summary table for IR spectral data (include original printouts with report)
Fully interpret the data on the IR spectrum and explain in detail how you determined
the structure of the unexpected product
Based on spectral analysis, comment on the purity of your product
QUESTIONS:
87
Experiment #7: Multi-step Synthesis of Fragrances

OVERVIEW:
Many commercially available fragrances contain benzyl ethers, such as methyl diantilis,
which can be synthesized from 3-ethoxy-4-hydroxy benzaldehyde (ethyl vanillin) and
methanol. Ethyl vanillin is a derivative of vanillin, which is the primary component of
vanilla extract. The fragrance industry mainly uses ethyl vanillin because it produces a
stronger note, or odor:
The presence of the phenol functionality on the ring gives the compound a warm
woody scent, similar to the odor of vanilla. Many perfume makers have experimented
with altering the position of the phenol, as well as substituting the phenol with other
functional groups to see what effect these substitutions might have on the odor of the
final product with odors ranging from citrus and fruity to musky and amber. In
fact, there are many industries solely devoted to organoleptic chemistry, or the
development of compounds that stimulate the olfactories and tantalize the taste buds.
This is just one illustration of how the physical properties of a compound can be changed
by modification of the structure. Chemists often synthesize a variety of compounds with
slight changes in structure, called derivatives, to explore how changing certain functional
groups affect the desired properties of each derivative. In this experiment, you will
explore how the structure of the aldehyde and alcohol used to make benzyl ethers can
affect the odor of the final product. You and your classmates will each synthesize a
benzyl ether derivative. All students will use Aldehyde B and Alcohol 2. :
88
You will perform a multi-step synthesis; a reduction followed by an etherification. You

will isolate and characterize the intermediate as well as the final product.
CHALLENGE:
Your challenge in this experiment is to carry out the multi-step synthesis of a benzyl
ether derivative and compare its scent to your classmates derivatives to determine
how the structure affects its odor.
The primary objective of this experiment is to conduct a synthesis composed of multiple
steps with characterization of the intermediates obtained. You will utilize the techniques
you have learned up to this point to complete this task. You will also learn how to use
TLC analysis as a method to monitor reaction progress. Concepts include reduction of a
carbonyl group and formation of an ether from two alcohols.
READ:
Operational Organic Chemistry, pp. 246-252 (Borohydride Reduction of Vanillin to
Vanillyl Alcohol; note procedural changes!)
(Heating Under Reflux), 692-700 (Recrystallization), 665-673 (Thin-Layer
Chromatography), 773-792 (Infrared Spectroscopy; also refer to pp.793-801 for
Characteristic Infrared Bands), 802-815 (Nuclear Magnetic Resonance
Spectrometry)
PRELAB:
Balanced equations for the multi-step synthesis for your starting materials, drawing
the structure of your intermediate and final products;
Mechanisms for reduction of your aldehyde and etherification with your alcohol
(separate from equations);
Calculate amounts you will need for 10 millimoles (mmol) of your starting materials
for the first step, and 5 mmol of reagents (including the intermediate product) for the
second step;
Theoretical yield for the intermediate and final products (based on 10 mmol and 5
mmol, respectively);
Table of reagents containing all starting materials and products, with the data for all
pertinent physical properties (MW, bp/mp, density, etc.);
89
PROCEDURE:
Part 1: Reduction of aldehyde
In a 125-mL Erlenmeyer flask equipped with a magnetic stir-bar, dissolve 10 mmol of
the aldehyde in 10 mL of methanol. Cool the flask in an ice-water bath set on a
magnetic stir plate. With stirring, add 0.4 grams sodium borohydride in small portions
(approximately a spatula-tip full).
Remove the flask from the ice-water bath and let the reaction mixture sit at room
temperature until the bubbling has subsided (~20-30 minutes).
Place the flask back in the ice-water bath and, with stirring, slowly add 10 mL of 3M
HCl. Check that the pH is 4. If not add more HCl until solution is sufficiently acidic.
Remove the flask from the ice-water bath and gently swirl until bubbling has
subsided.
Add 20 mL ethyl acetate to dissolve any solids and place the solution in a 125 mL
separatory funnel. Drain the organic layer into a clean Erlenmeyer flask.
Extract the organic layer two more times with 10 mL water then once with 10 mL
saturated sodium chloride solution. Separate the layers and place the organic layer in
a clean dry flask. Add magnesium sulfate to the organic layer with swirling until
solution is not cloudy. Gravity filter the solution into a round bottom flask and
evaporate the methylene chloride with the rotary evaporator.
Obtain a mass on the resulting product and move on to the next step with no further
purification.
Part 2: Etherification
Obtain the mass of your benzyl alcohol and calculate the yield. Be sure to save a
sample for IR and NMR analysis. After product is dry, weigh the flask to obtain the
yield.
Place 0.5 gram of Amberlyst 15 beads into a 100 mL round bottom flask equipped
with a magnetic stir bar. Wash the beads by adding 5 mL of the alcohol, swirling,
then carefully pouring as much of the alcohol as possible out of the flask. Repeat the
wash two more times.
Add 5 mL alcohol to the beads and add a magnetic stir bar to the flask. Dissolve 5
mmol of the product from step 1 in 5 mL of the alcohol and add to the solution
containing the beads.
Remove one drop of the mixture and save for TLC analysis (see How to Perform
TLC Analysis and section below). Attach a reflux condenser to the flask and reflux
for 15 minutes with stirring by magnetic stir plate.
Remove the flask from heat and let cool to room temperature. Remove one drop and
perform TLC analysis (see below). If reaction is not complete, replace heat source
and let reflux another 15 minutes. Let solution cool and remove another drop and
perform TLC analysis. Repeat process until reaction appears to be complete by TLC
analysis (that is, the starting benzyl alcohol no longer appears on the TLC plate).
After reaction is complete, allow solution to cool to room temperature. Gravity filter
the reaction mixture into a small beaker. Wash the round-bottom flask several times
90
with a few mL of methylene chloride and pour them onto the filter paper to wash the
beads thoroughly.
Transfer the solution to a separatory funnel and add 20 mL of methylene chloride.
Wash the organic solution three times with 10 mL distilled water.
Place the organic layer in a clean dry Erlenmeyer flask. With swirling, add enough
magnesium sulfate to dry the organic solution. Gravity filter the solution into a tared
round bottom flask. Remove the methylene chloride via rotary evaporation.
Obtain mass of your product before purification.
TLC analysis:
Dissolve each drop from the reaction mixture in 5 drops of acetone. Be sure to note at
which time the drop was removed from the solution (before reflux, after 15 minutes, after
30 minutes, etc.) On the TLC plate, place each of the spots in order. The lane for the first
drop is labeled as t=0, the next lane is labeled t=15, and so on. For the eluent, mix 5 mL
of ethyl acetate and 5 mL of hexane (1:1 ethyl acetate/hexane). Run the TLC plate as you
did in Experiment 1. To determine if the reaction is complete, examine the spots under
UV lamp. The spots for the starting materials in lane t=0 should not be present in the later
lanes. If there is still a significant amount of unreacted starting material present, continue
refluxing and testing by TLC until the reaction is complete. You may need to add more
acetone to the sample as it evaporates.
Part 3: Column Chromatography
Judge from your previous TLC results in this experiment what a good solvent mixture
for column chromatography would be.
Perform column chromatography on the impure benzyl ether, keeping in mind all the
details about this technique you learned in Experiment 3.
Make sure you keep ALL the fractions until TLC has been preformed on them and
you have isolated your pure benzyl ether.
Obtain the mass, IR and NMR of your final pure product.
LAB REPORT:
Balanced equation for the reduction of the aldehyde and subsequent acid-catalyzed
etherification
Mechanism for aldehyde reduction
Mechanism for acid-catalyzed etherification
Summary table with experimental yield, percent yield and mp where applicable for all
products
Summary table for IR spectral data (include original printouts with report)
Summary table for NMR spectral data (include original printouts with report)
Fully interpret the data on both the IR and NMR spectra, including:
o Compare the IR spectrum of your intermediate product and final product,
noting similarities and differences
o Compare the 1H-NMR spectrum of your intermediate product and final
product, noting similarities and differences
o Comment on purity of your products
Include a drawing of your TLC plate(s), labeling the spots and calculate the Rf values
91
Explain in detail how you determined the etherification reaction was complete
[The section below will not be completed this semester]
QUESTIONS:
92
Experiment #8: Enolate Chemistry Chalcone Synthesis

OVERVIEW:
Chalcones are molecular scaffolds of particular interest due to the variety of biological
activities associated with them, including cytotoxic, antitumor, anti-inflammatory,
antiplasmodial, immunosuppression, and antioxidant properties.1 They are intermediates
in the biosynthesis of flavonoids, which also have many potential pharmaceutical uses.
Chalcones are easily synthesized by the base-catalyzed aldol condensation of an aldehyde
and a ketone:
CHALLENGE:
Your challenge in this experiment is to design the synthesis, purification and
characterization of a chalcone derivative, using the concepts and skills learned
throughout the semester.
The primary objective of this experiment is to utilize the techniques learned up to this
point to synthesize, purify, and characterize a compound. The secondary objective is to
learn to use TLC analysis to determine optimal conditions for purification by column
chromatography. This experiment also illustrates carbonyl chemistry and aldol
condensations.
READ:
Operational Organic Chemistry, pp. 520-521 (Preparation of Aldol Condensation
Products; note procedural changes!); 847-848 (Planning an Experiment)
(Thin-Layer Chromatography), 656-664 (Liquid-Solid Column Chromatography),
773-792 (Infrared Spectroscopy; also refer to pp.793-801 for Characteristic Infrared
Bands), 802-815 (Nuclear Magnetic Resonance Spectrometry)
PRELAB:
Balanced equation for the aldol condensation;
Mechanism for the aldol condensation;
Calculate the amounts you will need of your starting materials (based on 3.0 mmol
limiting reagent);
Theoretical yield for final product (based on 3.0 mmol limiting reagent);
Table of reagents containing all starting materials and products, with the data for all
pertinent physical properties (MW, bp/mp, density, etc.);
93
PROCEDURE:
Obtain 3 mmol of 3-methoxyacetophenone and 3 mmol of 4methylbenzaldehyde (also called p-tolualdehyde). Dissolve in 30 mL methanol
and add 3 mL 3M NaOH.
Stir the solution vigorously under reflux conditions until the reaction is complete
(monitor by TLC).
When the reaction is complete, cool the solution to room temperature and remove
the solvent via rotary evaporator.
Add 40 mL methylene chloride and 10 mL H2O to the residue. Transfer to a
separatory funnel, shake, and separate the layers. If the layers do not separate, add
5 mL saturated NaCl.
Wash the organic layer with saturated NaCl (2 x 10 mL), dry over MgSO4, and
evaporate the solvent.
Purify the product by column chromatography. Use your TLC to determine an
appropriate eluent.
LAB REPORT:
Balanced equation for aldol condensation for your derivative;
Mechanism of aldol condensation;
Fully interpret the data on both the IR and NMR spectra, and include both printouts
with your report
Explain in detail how you purified your product (include TLC data if necessary)
Based on your data, comment on the purity of your product
Discuss in detail any problems you encountered during the experiment and how you
dealt with them
QUESTIONS:
94

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CHEMISTRY 237

University of Illinois at Urbana-Champaign

Prof. Steven C. Zimmerman

112 Chemistry Annex

263 Noyes Laboratory

FOR ANY SECTION CHANGES OR TO DROP

The Chemistry 237 Lab Manual is being made available by email

Operational Organic Chemistry. Lehman, J.W., 4th Ed., Pearson

Purchase at Illini Union Bookstore (809 S. Wright Street, Champ.)

Purchase at IUB, TIS, or Folletts. Aprons are not acceptable.

Chemical Education Resources Notebook (ISBN: 0875402488)

HGS Researcher Model Set Organic Chemistry B

Material on the examinations will be taken primarily from the

Criteria for Determination of Final Letter Grades

CHEM 237 Fall 2012

LAB: Finish Experiment 1 and Begin Experiment 2

LAB: Finish Experiment 2 and Begin Experiment 3

LAB: Finish Experiment 3

LAB: Begin Experiment 4

LAB: Finish Experiment 4 and Begin Experiment 5

LAB: Finish Experiment 5

LAB: Begin Experiment 6

LAB: Finish Experiment 6

LAB: Begin Experiment 7

THANKSGIVING WEEK BREAK

General Information: Procedures and Grading

Penalties for Laboratory Misconduct in CHEM 237

Warning (1st time), then 5 pts. off of lab report

Failing grade for the course

Excused absence (by instructor)

No penalty must make up lab, arrange with

Late lab report

15% of maximum value of lab report;

Failure to turn in any lab report

Failing grade for the course

Additional chemical samples

10 pts. off of lab report plus expelled from lab

Failure to wear proper attire

Sent out of lab until proper attire is worn

Improper waste disposal (including chemicals,

Warning (1st time), then 5 pts. off lab report

Improper dispensing of chemicals

Warning (1st time), then 5 pts. off lab report

Failure to close chemical bottles or carboy stopcocks

Warning (1st time), then 5 pts. off lab report

Improper glass disposal (including pipettes, vials,

Warning (1st time), then 5 pts. off lab report

Failure to turn off and unplug unused equipment

Warning (1sttime), then 5 pts. off lab report per

Negligent chemical spills

10 pts. off lab report per offense

Failure to maintain workspace (chemicals, wet bench

Warning (1st time), then 5 pts. off lab report

Laboratory Notebooks, Lab Reports, and Product

Guidelines for Laboratory Notebooks

Title of experiment and date;

During the experiment:

( ol 1< ~') /J.l tx)'l

c~ kC~ ,..;o ~.P ~u:

at t~. IC~ ,Cll. ~

let,,( lti~ ~() ~ t

r~ re~ ert i'f\C

[~7 ?-( ;~;: