DUHOK POLYTECHNIC UNIVERSITY

TECHNICAL COLLEGE OF ENGINEERING

PETROCHEMICAL ENGINEERING
DEPARTMENT.

CHEMISTRY II LABORATORY

Prepared by:
Assist. Prof. Dr. Shayma A. Shaker
1

Page

CONTENT
Experiment 1: reaction in aqueous solutions

Experiment 2: Le chateliers principle

Experiment 3: Buffer solutions

11

Experiment 4: Solubility product constant and common-ion effect

18

Experiment 5: The solubility of a salt in water at various temperatures

23

Experiment 6: Molecular geometries of covalent molecules: lewis

structures and VSEPR theory
Experiment 7: Ideal gas law

29

Experiment 8: Properties of alcohols: structure, reactions and

identification of alcohols
Experiment 9: Carboxylic acids reactions and derivatives

37

References

55

34

47

LAB EXPERIMENTS

EXPERIMENT 1
REACTION IN AQUEOUS SOLUTIONS
OBJECTIVES
1. Determine the species present in aqueous solutions of compounds using the
solubility rules.
2. Predict the type of the reaction that will occur when two aqueous solutions are
mixed.
3. Write the chemical equation, the ionic equation, and the net ionic equation for
reactions taking place between aqueous solutions.
INTRODUCTION
One of the most important characteristics of water is its ability to dissolve many
compounds. Solutions in which water is the solvent are called aqueous solutions.
Many important reactions take place in aqueous solutions. In fact, many of the
reactions that take place throughout your body (from your organs down to
individual cells) are aqueous reactions. Understanding the most common aqueous
reactions and how to correctly write them is one of the most important skills you
should master in Chemistry. One must ask the question: what observations indicate
that a chemical reaction has occurred? Some indications include: the formation of
an insoluble solid (precipitate), or color change, the evolution of a gas, or a
temperature change. In this experiment, you will predict what happen when two
aqueous solutions are mixed, and then test your prediction in laboratory.
In metathesis or double displacement reactions, cations and anions exchange
partners as in the following generic reaction:

There are three types of metathesis reactions - precipitation reactions, gas-forming

reactions, and neutralization reactions. The forth reaction that you will perform is
totally different because it is a type of an electron transfer reaction. Students must be
familiar with the solubility rules and be able to use then efficiently.

Table 1.1: Solubility Guidelines for Common Ionic Compounds in Water

Pre-lab questions
1. Write the molecular equation, ionic equation, and net ionic equation for the
following reactions:
a. Sodium chloride and ammonium nitrate.
b. Sodium sulfate and silver nitrate.
c. Sodium carbonate and barium nitrate.
d. Sodium hydroxide and barium nitrate.
2. Write the precipitation reaction equations in (part I) and predict your observation.
Table 1.2: Chemical and Supplies

Procedure
Part I: Precipitation Reactions
1. To the 1st row that labeled Na2SO4, number its test tubes 1-2.

2. Place 1 mL of o.1 M Na2SO4 into the two test tubes

using the pipette.
3. To Na2SO4 solution in test tube #1, add 1 mL of 0.1M
of NH4NO3 and record your observation.
4. To Na2SO4 solution in test tube #2, add 1 mL of 0.1M
of AgNO3 and record your observation.
5. To the 2nd row that labeled NaOH, number its test tubes 1-2.
6. Repeat steps 2-4.
7. To the 3rd row that labeled Na2CO3, number its test tubes 1-2.
8. Repeat steps 2-4.
9. Clean all the glass wares before starting part II.
Part II: Gas-Formation Reaction
1. Add to a dry test tube a few grams of CaCO3.
2. Add 1 mL of water to step 2.
3. Add 1 mL of 2 M HCl to the test tube and record your observation.
4. Repeat steps 1-3 using Na2SO4 instead of CaCO3.
Part III: Neutralization Reaction
1. Use 250 mL beaker and weigh about 0.5 grams of Mg(OH)2.
2. Use the graduated cylinder to measure 25.0 mL of water.
3. Add 1-2 drops of phenolphthalein indicator to the beaker in step 1.
4. Add the 25 mL of water that you measured in step 2 to the
250 mL beaker.
5. Use another graduated cylinder to measure 25 mL of HCl.

6. Add HCl to the 250 mL beaker in step 1 and thoroughly

stir the solution.
7. Record your observation.
Part IV: Oxidation-Reduction Reaction
Note: this reaction must be performed inside the hood
1. Put a small piece of copper wire in one of the test tubes.
2. Use the graduated cylinder to measure 5 mL of 6.0 M HNO3.
3. Transfer HNO3 solution in step 2 to your test tube in step 1.
4. Record your observation.
Table 1.3: Recording the Reaction Observations

Balanced Chemical Equation

Write a balance net ionic equation for each part (Ignore part IV).
Conclusion
Explain in one or two paragraphs if you were able to achieve the objectives of this
experiment.
If it is not, please explain your weakness.

EXPERIMENT 2
LE CHATELIERS PRINCIPLE
OBJECTIVE

To study equilibrium system and their responses to stress as described by Le

Chateliers principle.

INTRODUCTION
Most chemical reactions do not produce 100 percent yield of product, not because of
experimental technique or design, but rather because of the chemical characteristics of
the reaction itself. Initially, the reactants produce the expected products, but after
some time the concentrations of the reactants and products become constant i.e. stop
changing. When this happens, the system is in a state of dynamic equilibrium.
Equilibrium is a state where there are no observable changes as time goes by. At
equilibrium, the rate of the forward reaction is equal to the rate of the reverse reaction.
If the concentration of one of the species in the equilibrium system changes, or
if the temperature changes, the equilibrium tends to shift in a way that compensates
for the change. According to Le Chateliers principle, when an external stress is
applied on a system at equilibrium, the system responds in such a way that the stress
is partially offset as the system reaches a new equilibrium position. Equilibrium will
be reestablished at a different point that is, with different concentrations of reactants
and products. External stress can be changes in concentration of reactant or product,
changes in volume and pressure (for gaseous systems) and changes in temperature.
Adding a catalyst does not shift the position of an equilibrium system however, its
presence makes the system reach equilibrium sooner. A well-known example of
equilibrium is the chromate(VI)-dichromate(VI) system. When solid potassium
chromate, K2CrO4 is dissolved in water it forms a yellow solution. When solid
potassium dichromate, K2Cr2O7 is dissolved in water the resulting solution is
orange. The colors come from the negative ions: CrO42-(aq) and Cr2O72-(aq). In
solution these 2 ions are actually in equilibrium with one another.

A solution of chromate ions

A solution of dichromate ions
Their equilibrium can be shifted forward or reverse by adding either H+ ion or OH
ion.
APPARATUS
Beaker, graduated cylinder, test tubes, test tube rack and Beral pipette.
7

CHEMICALS
0.1M FeCl3 solution
0.1M K2CrO4 solution
1M NaOH solution

0.1M KSCN solution

0.1M K2Cr2O7 solution

0.1M KCl solution

1M HCl

PROCEDURE
1. Using a Beral pipette, place 10 drops of 0.1M FeCl3 into a beaker. Add 10 drops
of 0.1M KSCN to the same beaker. Dilute the content of the beaker with distilled
water until the solution has a light reddish-orange color.

2. Label four test tubes 1 - 4 and stand them in a test tube rack.
3. Place 10 drops of the reddish-orange solution into each of the 4 test tubes. Set test
tube 1 at one end of the rack (to be used for color comparison).
4. Using a clean Beral pipette, add 0.1M FeCl3 drop by drop to the solution in test
tube 2 until a color change occurs. Record your observation.
5. Repeat step 4, but instead of FeCl3 add the following solutions drop by drop to the
test tube indicated. Rinse the pipette after each use.
Test tube 3
Test tube 4

0.1M KSCN
0.1M KCl

6. Discard the solutions in the 4 test tubes. Wash and rinse the test tubes.
8

7. Number four test tubes from 5 to 8. Stand the test tubes in the rack.
8. Place 10 drops of 0.1M K2CrO4 each into test tubes 5 and 6. Place 10 drops of
0.1M K2Cr2O7 each into test tubes 7 and 8.
9. Use a clean Beral pipette to add 1M HCl drop by drop to test tube 5 until the color
changes. Record your observation.
10. Repeat step 9 with test tube 6. As soon as the color changes, rinse the pipette and
use it to add 1M NaOH drop by drop to the solution until the color changes again.
Record your observations for this step.
11. Use a clean dropper pipette to add 1M NaOH drop by drop to test tube 7 until the
color changes. Record your observation.
12. Repeat step 11 with test tube 8. As soon as the color changes, rinse the pipette and
use it to add 1M HCl to the solution until the color changes again. Record your
observation.

REPORT SHEET EXPERIMENT 2: LE CHATELIERS PRINCIPLE

Name : ___________________________

Student ID.: ________ Locker #: ____

Partner : __________________________

Student ID.: ________ Locker #: ____

Section : ____________

Date of experiment: _______________

OBSERVATION AND DATA

Colour of solution
Test tube 2:

____________________________________________

Test tube 3:

____________________________________________

Test tube 4:

____________________________________________

Colour Changes of solution

Test tube 5:

____________________________________________

Test tube 6:

____________________________________________

Test tube 7:

____________________________________________

Test tube 8:

____________________________________________

PRE-LABORATORY QUESTIONS
1.

Write the equilibrium equation for the reversible reaction that takes place in
step 1.

2.

Using the Le Chateliers principle, explain your observation when FeCl3 is

added to the solution in test tube 2 (step 4) and similar explanations for the
addition of KSCN and KCl to test tubes 3 and 4 respectively (step 5).

3.

Using the equilibrium equation for the reaction and Le Chateliers principle,
explain the color changes in the K2CrO4 and K2Cr2O7 solutions upon the
addition of acid and base (test tubes 5 8).

10

EXPERIMENT 3
BUFFER SOLUTIONS

INTRODUCTION
Any solution that contains both a weak acid HA and its conjugate base A in
significant amounts is a buffer solution. A buffer is a solution that will tend to
maintain its pH when small amounts of either acid or base are added to it. Buffer
solutions can be made to maintain almost any pH, depending on the acid-base pair
used. The pH of a buffer solution is determined by the Ka of the acid and by the ratio
of concentrations of HA and A. This can be calculated by rearranging the
expression for the Ka of the conjugate acid of the buffer:
[H O+ ][A ]
[HA]
Becomes
Ka = 3
[H3O+ ] = K a
[HA]
[A ]
The rearranged equation shows that the H3O+ ion concentration of the buffer solution
can be found by multiplying the Ka of the acid by the ratio of the molar
concentrations of the two components. To solve directly for the pH of the buffer, the
equation can be put into logarithmic form. If the above equation is rearranged and the
negative log of both sides is taken, a new form of the equation known as the
Henderson-Hasselbalch equation results.

[A ]
Henderson-Hasselbalch equation
[HA]
A buffer solution can maintain its approximate pH when an acid or a base is
added to it because it can react with both acids and bases. If a strong acid (H3O+) is
added, the basic component of the buffer (A) can react with it, and if a strong base
(OH) is added, the acidic component of the buffer (HA) will react with it.
H3O+ (aq) + A (aq) HA (aq) + H2O (l)
OH (aq) + HA (aq) H2O (l) + A (aq)
In this way, any strong acid or strong base that is added to the buffer solution is
converted into a weak acid or weak base. The ratio of weak acid to weak base
changes, which causes the pH to change slightly, but not drastically.
Buffer solutions are most effective when both components, the conjugate acid
and the conjugate base, are present in reasonably large concentrations. If this is the
case, the buffer is said to have a high buffer capacity. Also, a buffer is most effective
when there are approximately equal concentrations of the two buffer components
(a ratio of [X]/[HX] close to 1/1) because in this case the solution will guard against
large pH changes equally well whether acid is added or base is added.
In order for the solution to be considered a buffer, this ratio must be between a
1/10 and a 10/1 ratio of [X-]/[HX]. This restriction means that the [H3O+] in the
buffer will be within a factor of 10 of the Ka value of the conjugate acid. It also
means that the pH of the buffer will be within one pH unit of the value of the pKa of
the conjugate acid. For example, suppose you wanted to make a buffer containing
pH = pKa + log

11

phosphoric acid (H3PO4) and dihydrogen phosphate (H2PO4). Since the Ka of

H3PO4 is 7.5 10-3 and the pKa is 2.12, as shown in the table below, the pH of this
buffer would have to be between 1.12 and 3.12. If you wanted to make a buffer with
a pH outside of this range, you would have to choose a different conjugate acid-base
pair.
Buffer Solutions That Can Be Made With H3PO4 and H2PO4
[H3PO4 ]
Ka
pKa [H2 PO4 ]
[H PO ]
[H3O+ ] = K a
pH = pKa + log 2 4

[H2 PO4 ]
[H3PO4 ]
[H3PO4 ]
1.12

1/1

7.5 102
7.5 103

10/1

7.5 104

3.12

1/10
7.5 103

2.12

2.12

In this experiment, you will be assigned a pH value, and you will prepare a
buffer solution having that pH. There will be two sets of acid-base pairs available in
the lab. These are:
1. Acetic acid (CH3CO2H, Ka = 1.8 105) and sodium acetate (NaC2H3O2).
2. Ammonium chloride (NH4Cl, Ka for NH4+ = 5.6 1010) and ammonia
(NH3).
The buffer will be prepared by choosing the appropriate acid-base pair, calculating the
molar ratio of acid to base that will produce the assigned pH, and then mixing the
calculated amounts of the two compounds with enough deionized water to make 200.
mL of buffer solution.
A solution with approximately the same pH as the buffer solution will be
prepared by diluting a solution of a strong acid or a strong base. This solution will not
be a buffer solution, as can be shown by comparing its buffering ability to that of the
buffer solution. Finally, a known amount of strong acid or base will be added to the
buffer solution. Before adding this acid or base, the pH change that the addition
should cause will be calculated. The observed pH change will be compared to the
calculated value.
PROCEDURE
SAFETY PRECAUTIONS:
Wear your SAFETY GOGGLES.
Use the
concentrated acetic acid and ammonia solutions in the FUME HOOD. If any acid or
base solution splashes on your skin, wash it off immediately with copious amounts of
running water.
WASTE DISPOSAL: All waste from this experiment should be poured down the
drain, followed by plenty of running water.

12

Part 1 - Preparing the Buffer Solution

Prelab Calculations
1. Obtain a pH assignment from your instructor.
2. Decide which of the two available buffer systems you should use.
3. Determine the ratio of [A]/[HA] needed in the buffer.
4. Which component will be more concentrated, A or HA? Choose a value for the
concentration of that component anywhere in the range 0.2 0.6 M. Calculate
what the concentration of the other component should be.
5. Calculate the volume (in mL) of 17.5 M CH3CO2H or 14.8 M NH3 needed to
make 200 mL of your buffer.
Calculate the mass (in g) of solid
NaCH3CO23H2O or NH4Cl needed to make 200 mL of your buffer.
PROCEDURE
Measure out the amounts of the buffer components needed, add them to about
100 mL of deionized water in a 250-mL Erlenmeyer flask. Swirl until all the solids
are dissolved. Pour the mixture into a large graduated cylinder, and dilute it to a total
volume of 200 mL. Pour it back and forth between the graduated cylinder and your
flask so that it is thoroughly mixed. Store the buffer solution in the flask.
Set up a pH meter at your desk and calibrate it according to the instructions.
Remember that the electrode of the pH meter is FRAGILE! Also, remember to rinse
the electrode off with deionized water when transferring it between different
solutions.
Pour about 50 mL of your buffer solution into a small beaker and measure the
pH. The pH of the solution should be close to the expected value but might not be
exactly the same. A minor discrepancy will not affect the results of the remainder of
the experiment.
There are several possible reasons for the pH meter reading being different
from the expected pH. One is that some of the volatile component of your buffer may
have escaped from the solution into the air. Another is the fact that the Ka values for
acids vary with temperature. The values usually reported are accurate for 25C.
Part 2- Preparing a Solution with the Same pH by Dilution of a Strong Acid or
Base
The pH of a typical acetic acid-acetate buffer solution is between 4 and 5. A
solution with a pH in this range can easily be prepared by diluting a solution of strong
acid, such as HCl, until the hydronium ion concentration is between 104 and 105
M. Similarly, a typical ammonium ion-ammonia buffer solution has a pH between 9
and 10. A dilute solution of NaOH with [OH] between 104 and 105 M will also
be in this pH range. These solutions, however will not act as buffer solutions. In this
section of the experiment, you will prepare a solution with approximately the same
pH as your buffer solution by diluting a more concentrated solution of strong acid or
base.

13

Prelab Calculations
If your buffer is acidic, calculate the volume (in mL) of 0.0010 M HCl needed to
prepare 100 mL of a solution that has the same pH as your buffer.
If your buffer is basic, calculate the volume (in mL) of 0.0010 M NaOH needed to
prepare 100 mL of a solution that has the same pH as your buffer.
PROCEDURE
Prepare your unbuffered solution, by diluting the calculated amount of 0.0010
M HCl or 0.0010 M NaOH solution to a final volume of 100 mL. Measure its pH.
Again, the reading on the pH meter may not display the pH expected for the solution.
The pH of solutions as dilute as this can be affected by small amounts of impurities,
including CO2 dissolved in the water. The pH can be adjusted if desired, but the
comparison of this solution to the buffer solution will work even if the pH values of
the two are not the same.
Part 3 - Comparing the Buffering Abilities of the two Solutions
PROCEDURE
To test the buffering abilities of the solutions, 0.1 M HCl or 0.1 M NaOH will
be added. If the solutions are acidic, add 0.1 M NaOH, and if they are basic, add 0.1
M HCl.
Place the pH electrode in the 50 mL of buffer solution tested earlier. Remeasure the pH, then add 5 drops of 0.1 M NaOH or 0.1 M HCl solution (see above).
Carefully swirl the solution, making sure not to bump the electrode, and record the
new pH. Repeat the procedure with another 5 drops of NaOH or HCl. How much did
the pH change upon the addition of these amounts of HCl or NaOH?
Rinse off the electrode with deionized water, place it in the nonbuffered
solution, and measure the pH. Follow the same procedure as you used for the buffer
solution. Add 5 drops of drops of HCl or NaOH, and record the new pH. Add 5 more
drops, and record the pH. It is important to follow the same procedure so that you can
more accurately compare the two solutions. How much did the pH change for the
unbuffered solution? How do the pH changes compare for the buffered and
unbuffered solutions?
Part 4 - Changing the pH of a Buffer Solution
The pH of a buffer solution does change when large amounts of strong acid or
strong base are added to it. Addition of strong acid uses up the conjugate base of the
buffer, and addition of strong base uses up the conjugate acid. The pH of the buffer
changes because the ratio of conjugate acid to conjugate base has been changed.
In this part of the experiment, enough 1.0 M HCl will be added to 100. mL of
the buffer solution to react with half of the conjugate base in the solution. The
observed change in pH will be compared to the pH change expected on the basis of
the prelab calculation.

14

Prelab Calculations
1. How many moles of base (NH3 or C2H3O2) are in 100 mL of the buffer solution
you prepared? What is half of this amount? This is the number of moles of HCl
that you will add to the solution.
2. Calculate the volume (in mL) of 1.0 M HCl needed to supply this number of
moles. That is the amount needed to react with half of the conjugate base in 100
mL of your buffer solution.
3. What should the pH be after this amount of HCl is added? What is the expected
change in pH of the buffer?
PROCEDURE
Add this volume of 1.0 M HCl to 100 mL of the buffer solution, and measure
the pH. Record the change in pH. Compare the expected (calculated) pH change to
the actual pH change of the buffer.
Sample Calculations
Part 1 Preparing a Buffer Solution
Sample calculations will be done for an assigned pH of 2.50.
A pH of 2.50 corresponds to a [H3O+] = 102.50 = 3.162 103 M.
Phosporic acid (H3PO4) and sodium dihydrogen phosphate (NaH2PO4) could be
used to make this buffer, because Ka for H3PO4 (Ka = 7.5 103) is close to the
desired [H3O+].
Ka
7.5 10 3
[H 2PO4 ]
[H 2PO4 ]
The
ratio should be
=
=
=
[H3PO4 ]
[H3PO4 ]
[H3O+ ]
3.162 103
2.372
1
H2PO4 will be the most concentrated component of this buffer system. We
will arbitrarily choose its concentration to be 0.50 M. This means that the
concentration of H3PO4 should be 0.50 M 2.372 = 0.2108 M
To make 200 mL of the buffer solution, we will need to measure out a certain
volume of concentrated phosphoric acid, which is available as a 14.7 M aqueous
solution. And we will need to weigh out a certain mass of sodium dihydrogen
phosphate, which is available as the hydrated solid, NaH2PO42H2O (the waters of
hydration are included in the molar mass).
To make 200 mL of a 0.2108 M phosphoric acid solution,
0.2108 M
200 mL
= 2.87 mL of concentrated phosphoric acid needed.
14.7 M
To make 200 mL of a 0.50 M sodium dihydrogen phosphate solution,
0.50 mol 156.0 g
0.200 L

= 15.60 g of NaH2PO42H2O needed.

L
mol

15

So, to prepare the buffer solution, we will mix 2.87 mL of concentrated

H3PO4 and 15.60 grams of NaH2PO42H2O with enough water to make 200 mL of
solution.
Part 2- Preparing a Solution with the Same pH by Dilution of a Strong Acid or
Base
To make 100 mL of a solution with pH = 2.50 ([H3O+] = 3.162 103 M),
we will dilute a 0.10 M HCl solution. (Note, in your experiment, you will be diluting
an 0.0010 M HCl solution or an 0.0010 M NaOH solution.)

3.162 103 M
= 3.16 mL of 0.10 M HCl needed
0.10 M
So, to prepare the unbuffered solution, we will mix 3.16 mL of 0.10 M HCl
with enough water to make 100 mL of solution.
100 mL

Part 4 - Changing the pH of a Buffer Solution

We will take 100 mL of the buffer solution, and add enough 1.0 M HCl to
react with half of the moles of H2PO4, the conjugate base.
0.50 mol
0.100 L
= 0.050 moles of H2PO4 are present in 100 mL
L
0.025 moles of H2PO4 will be react with 0.025 moles of HCl.
L
0.025 mol HCl
= 0.025 L or 25 mL of 1.0 M HCl will be added.
1.0 mol
So, to change the pH of our buffer solution, we will take 100 mL of our
original buffer solution, and add 25 mL of 1.0 M HCl to it.
All of the added HCl will react with the H2PO4. Some H2PO4 will be used
up, and more H3PO4 will be formed.
H3O+ (aq) + H2PO4 (aq) H3PO4 (aq) + H2O (l)
Before reaction
0.025 mol
0.050 mol
0.021 mol
lots
0.025 mol 0.025 mol
+0.025 mol
After reaction
0
0.025 mol
0.046 mol
(7.5 10 3 )(0.046)
(moles H3 PO4 )
=
= 1.38 102 M

(0.025)
(moles H 2 PO4 )
So, after the addition of HCl, the new pH will be log (2.01 102) = 1.86.
The expected change in pH will be 1.86 2.50 = 0.64 pH units.
+

[H3O ] = K a

Additional Questions (for the finished lab report)

1.
For each of these desired pH values, choose a weak acid-conjugate base pair
from your textbook that could be used to prepare a buffer solution with that pH.
Calculate the desired [A]/[HA] ratio in each case.
(a) pH = 6.00
(b) pH = 8.00
(c) pH = 11.00

16

2.

500 mL of a buffer solution contains 0.050 mol NaHSO3 and 0.031 mol
Na2SO3.
(a) What is the pH of the solution?
(b) Write the net ionic equation for the reaction that occurs when NaOH is
added to this buffer.
(c) Calculate the new pH after 10. mL of 1.0 M NaOH is added to the buffer
solution.
(d) Calculate the new pH after 10. mL of 1.0 M NaOH is added to 500. mL of
pure water.
(e) Explain why the pH of the water changed so much as compared to the pH of
the buffer.

17

EXPERIMENT 4
SOLUBILITY PRODUCT CONSTANT AND COMMON-ION EFFECT
OBJECTIVES
a. To determine the molar solubility and Ksp of Ca(OH)2.
b. To determine the molar solubility of Ca(OH)2 in the presence of added Ca+2.
Theory:
Many common ionic compounds, which have a very limited solubility in
water, are called slightly soluble salts. A saturated solution of a slightly soluble ionic
compound produces a dynamic equilibrium between the compound and the
dissociated ions. However, because the compound is only slightly soluble, the
solution has a low concentration of ions. For example, in a saturated BaSO4 solution,
the equilibrium between BaSO4 (s) and the Ba+2(aq) and SO4-2 (aq) ions lies far to the left
because of its low solubility:
BaSO4 (s) Ba+2(aq) + SO4-2 (aq)
The equilibrium expression for this reaction is:
[Ba +2 ][SO4 2 ]
K=
[BaSO4 ]
Since in a heterogeneous equilibrium the concentration of solid BaSO4 is a constant
for a given temperature, we can rewrite the expression as:

K sp = K[BaSO4 ] = [Ba +2 ][SO4 2 ]

Ksp is called the solubility product constant or, more simply, the equilibrium constant
of a slightly soluble ionic compound.
The small Ksp value for BaSO4, 1.5x10-9, means that in pure water the molar
concentration of Ba+2 equals the molar concentration of SO4-2 and each equals 3.9
x10-5 mol/L as shown below:
Ksp = [Ba+2][SO4-2] = 1.5x10-9
BaSO4 (s) Ba+2(aq) + SO4-2 (aq)
Initial
excess
0
0
Change
-x
+x
+x
Equilibrium excess
x
x
Ksp = [Ba+2][SO4-2] = 1.5x10-9 = [x][x]
x = [Ba+2] = [SO4-2]
x2 = 1.5x10-9
x = 3.9 x10-5 mol/l = [Ba+2] = [SO4-2]

18

The molar solubility of BaSO4 also equals 3.9x10-5mol/L, because one mole of
BaSO4 must dissolve to produce one mole of Ba+2 and one mole of SO4-2 in solution.
What happens to the solubility of a slightly soluble compound when an ion, common
to the compound, is added to the saturated solution? According to Le Chatelier's
Principle, the position of the equilibrium shifts to use up the added ions and it shifts to
favor the formation of the solid compound. This reduces the compounds molar
solubility.
If 0.0010 mol SO4-2/L is added to a saturated BaSO4 solution, the added SO4-2 shifts
the equilibrium to the left, reducing the [Ba+2], and increasing the amount of solid
BaSO4.
BaSO4 (s) Ba+2(aq) + SO4-2 (aq)
Initial
excess
0
0.0010M
Change
-x
+x
+x
Equilibrium excess
x
0.0010M + x
Ksp = [Ba+2][SO4-2] = 1.5x10-9 = [x][0.0010 + x]
Assuming [x]++ 0.0010M
[ Ba + 2 ] = x =

K sp
2

[ SO4 ]

1.5 x10 9
= 1.5 x10 6 mol / L
0.0010

The molar solubility of BaSO4 equals the molar concentration of Ba+2. The molar
solubility of BaSO4 decreased from 3.9 x10- 5 mol/L to l.5 x10-6 mol/L. This
experiment determines the Ksp and molar solubility for Ca(OH)2.
Ca(OH)2 (s) Ca+2(aq) + 2 OH-1 (aq)
Ksp = [Ca+2][OH-1]2
A saturated Ca(OH)2 solution is filtered to remove solid Ca(OH)2 and the OH-1 ion is
titrated with a standard HCl solution to determine the number of moles and its
concentration. According to the equation for each mole of Ca(OH)2 that dissolves, one
mole Ca+2 and 2 moles OH-1 are present in solution. Thus by finding the [OH-1], the
[Ca+2], Ksp and molar solubility of Ca(OH)2 can be calculated. The molar solubility of
Ca(OH)2 = [Ca+2] = 1/2 [OH-1].
The pH of the saturated solution is measured which allows an additional
means to calculate the equilibrium [OH-1] and then calculate the [Ca+2], Ksp and molar
solubility.
We use the same procedure to determine the molar solubility of Ca(OH)2 with
+2
Ca added (an ion common to the slightly soluble salt equilibrium). However, since
Ca+2 is added from an external source [Ca+2] 1/2 [OH-1]. The [Ca+2] is determined
by the concentration added from the external source. The [OH-1] is determined by the
dissolving of the Ca(OH)2 so the molar solubility of Ca(OH)2 = 1/2 [OH-1].

19

PROCEDURE:
It is important to keep the bottles containing the Ca(OH)2 tightly capped when
not in use to prevent the solution from absorbing CO2. The reaction of carbonic acid
with the hydroxide ion will reduce the hydroxide ion concentration and will
precipitate CaCO3.
Part 1. Ksp and Molar Solubility of Ca(OH)2
1. Prepare a 50-mL burette for titration. Rinse the clean burette and tip with two
5-mL portions of standardized HCl solution and discard. Fill the burette with
standardized HCl, remove the air bubbles in the tip, and record the initial
volume ( 0.01mL).
2. Record the molarity of the HCl solution.
3. Rinse a 50-mL pipet with 1 or 2 mL of the saturated Ca(OH)2 solution and
discard.
4. Pipet 50.00 mL of the filtrate into a clean 125-mL Erlenmeyer flask and add 4
drops of bromthymol blue indicator. Record the solution's temperature.
5. Titrate with the standard HCl solution. Record the final volume ( 0.01mL)
needed to just turn the solution color from blue to yellow.
6. Repeat the titration with two new samples of Ca(OH)2.
Part 2: Molar Solubility of Ca(OH)2 in the presence of Ca+2
Repeat Part I, steps 2 - 3, using the saturated Ca(OH)2 solution to which 0.100M
+2
Ca has been added.

20

SOLUBILITY PRODUCT CONSTANT AND COMMON-ION EFFECT

Name:_________________________________________ Period:_________
Lab Partner:____________________________________ Course:_________
Data Table
Part 1: Ksp and Molar Solubility of Ca(OH)2
Trial 1

Trial 2

Trial 3

Trial 1

Trial 2

Trial 3

Temperature of solution (o C)
Buret reading, final (mL)
Buret reading, initial (mL)
Volume HCl used (mL)
Concentration of standard HCl solution (M)
Mole HCl added
Mole OH-1 in saturated Ca(OH)2 solution
Volume of saturated Ca(OH)2 solution (L)
[OH-1] at equilibrium (mol/L)
[Ca +21 at equilibrium (mol/L)
Ksp of Ca(OH)2 from the titration
Average Ksp of Ca(OH)2 from the titration
Molar solubility of Ca(OH)2 from the titration
Part 2: Solubility of Ca(OH)2 in presence of Ca+2
Temperature of solution (o C)
Buret reading, final (mL)
Buret reading, initial (mL)
Volume HCl used (mL)
Concentration of standard HCl solution (M)
Mole HCl added
Mole OH-1 in saturated Ca(OH)2 solution
Volume of saturated Ca(OH)2 solution (L)
[OH-1] at equilibrium (mol/L)
Molar solubility of Ca(OH)2
CALCULATIONS
Show your calculations for one trial from the titrations from Part 1 and Part 2 on a
separate sheet of paper and attach it to the report.
QUESTIONS:
1. How does the addition of CaCl2 affect the molar solubility of Ca(OH)2?
2. a. If some solid Ca(OH)2 is transferred into the titrating flask in Part 1, will the Ksp
value for Ca(OH)2 be higher or lower than the accepted value? Explain.

21

b. Will the molar solubility be higher or lower than the accepted value for
Ca(OH)2? Explain.
3. If the endpoint of the titration is overrun in Part 1, will the Ksp value for
Ca(OH)2 be higher or lower than the accepted value? Explain.
4. If the original Ca(OH)2 solution is not saturated in Part 1, will the Ksp value for
Ca(OH)2 be higher or lower than the accepted value? Explain.
5. The temperature was recorded in this experiment. Does the molar solubility of a
compound generally increase or decrease with increasing temperature dependent?
Explain.
PRELAB QUESTION
1. Write the Ksp expression for equilibria of these slightly soluble compounds in
aqueous solution:
a. Ag2CrO4 (s) 2Ag+1 (aq) + CrO4-2 (aq)

Ksp =

b. CaCO3 (s) Ca+2 (aq) + CO3-2 (aq)

Ksp =

c. Mg3(PO4)2 (s) 3 Mg+2 (aq) + 2 PO4-3 (aq) Ksp =

2. a. Calculate the molar solubility of PbCrO4.
Ksp = 1.8 x 10- 14
b. Calculate the molar solubility of PbCrO4 in the presence of 0.020 M Na2CrO4.
3. The pH of a saturated Mg(OH)2 solution is 10.46.
a. Calculate the [OH-1] in the solution.
b. Calculate the [Mg+2] in the solution.
c. Calculate the Ksp of Mg(OH)2.
4. Explain how the OH-1 molar concentration is determined in this experiment.
5. Explain how the Ca+2 molar concentration is determined in Part I of this
experiment.

22

EXPERIMENT 5:
THE SOLUBILITY OF A SALT IN WATER AT VARIOUS TEMPERATURES
OBJECTIVE
To measure the solubility of a salt in water over a range of temperatures and to
construct a graph representing the salt solubility.
INTRODUCTION
One of the most common forms of a homogeneous mixture is a solution. The one
component of a solution, which is usually present in the greatest proportion, is called
the solvent. The other components, present on a smaller scale, called solutes, are
considered to be dissolved in the solvent. There are a number of different kinds of
solutions: gases in gases (example: air), liquid in liquids (example: gasoline), gases in
liquids (example: carbonated soft drinks), solids in solids (example: alloys such as
brass), and solids in liquids (example: salt water). This experiment will involve a
solution formed with a solid solute (a chemical salt) and a liquid solvent (water). If
the properties of a solution remain constant, the system of solute and solvent is
considered to be at equilibrium. Obviously, if the solid is disappearing in to the
solvent, the system is not at equilibrium. Solubility of a solid in a liquid is dependent
on temperature, thus, at a given temperature, only a certain maximum amount of
solute will dissolve in a given amount of solvent. Beyond that amount of solute, no
more will dissolve and excess solute will remain in the solid form, settling to the
bottom of the solution container. This maximum amount of dissolved solute,
expressed quantitatively, is given in units of grams of solute/100 g of solvent. Such a
solution is termed a saturated solution, since it is holding all the solute it can hold at
that temperature. Experiments show that when excess solute is in contact with a
saturated solution, equilibrium is established in which solute continually dissolving in
amounts just equal to the solute is separating from solution (crystallization) (see
Figure 1). When saturated solutions of solid solutes are prepared at elevated
temperatures and then permitted to cool, the excess solute usually separates from the
solution by crystallizing. However, if a saturated solution is prepared at an elevated
temperature and any excess, undissolved solute is removed, crystallization often does
not take place when the solution is allowed to cool undisturbed. The solution can
contain more of the solute than normally is held in equilibrium with the solid state.
Such solutions are said to be supersaturated. A supersaturated solution is a system in a
metastable (unstable) condition. Agitation of the solution or the addition of a seed
crystal of the solute may start crystallization of the excess solute. After crystallization,
a saturated solution remains. In general, when a solution, which is nearly saturated
with a solid solute is cooled, a temperature is reached at which the solution becomes
saturated. On further cooling, the excess solute will crystallize, and will appear as
particles separated from the solution. For solutions of various salts in water it has
been found that temperature effects on solubility vary from salt to salt. Salts are
usually more soluble at elevated temperatures than at lower temperatures. In addition,
the change in solubility for a given salt, say between 20 and 30C, may not be the
same as the change in its solubility between 50 and 60C. To fully characterize the
solubility properties of a salt of interest, the chemist must gather data from
experimental measurements, such as those described in the next section.

23

Figure 5.1. The solution process

APPARATUS AND CHEMICALS
Potassium chlorate, KClO3, or potassium nitrate, KNO3 ice, large test tube, 25 x 200
mm
clamps: utility and thermometer, Bunsen burner, copper or nichrome wire (for stirrer)
110C thermometer or temperature probe and computer, distilled water, 10-mL
graduated cylinder, beaker, 250 or 400 mL,ring stand
SAFETY PRECAUTIONS
Potassium chlorate and potassium nitrate are oxidizers; do not allow them to come in
contact with combustible materials. Dispose of excess material in the appropriate
waste container. Do not throw any solid material in the trash.

PROCEDURE
Assemble the apparatus as shown in Figure 2. The preferred set-up uses a
thermometer clamp to hold the thermometer or temperature probe. If a thermometer
clamp is not available, place the thermometer in a split one-hole rubber stopper and
support it using a utility clamp. The thermometer is adjusted so that the bulb is
between 1 and 2 cm from the bottom of the large test tube. Make sure you have a
clear view of the temperature scale between 20 and 100C. To prepare the wire
stirrer, bend a loop in one end of the wire slightly smaller than the inside diameter of
the tube and bend it at a 90 angle to the wire. The wire loop should be positioned
around the thermometer bulb. Note: Once the apparatus is assembled, it is not to be
taked apart until the experiment is completed. Select a salt to use, either potassium
chlorate, KClO3, or potassium nitrate, KNO3. Weigh out the stated amount of salt
listed in Table 1. Record the mass of salt used, and add it to the clean dry test tube.
Measure the suggested amount of water in a 10-mL graduated cylinder (see Table 1 24

assume that 1 gram of water has a volume of 1 mL). Obtain the exact mass of water
by weighing the 10-mL graduated cylinder and the water, adding the water to the test
tube containing the salt, and reweighing the empty, but wet, graduated cylinder. The
difference between the mass of the graduated cylinder and water and mass of the
empty cylinder is the mass of water added. This procedure will be followed for each
addition of water for subsequent trials. Heat the test tube and its contents, stirring
while you heat. Continue heating until all of the salt has dissolved, but DO NOT
ALLOW THE SOLUTION TO BOIL. If the temperature is approaching 100C, and the
salt has not dissolved completely, stop heating, obtain 1 mL of water, weight it
according to the procedure in the step above, and add it to the test tube. The first
addition of water will be the sum of the two masses of water added. When all of the
salt has dissolved, stop heating and continue to stir. Watch the solution as it cools for
the appearance of small crystals of salt. When crystals first appear, note the
temperature of the solution and record it.

Figure 5. 2. Set-up for measuring solubility of a salt

Table 5.1.Quantites of salt and water

Add another portion of water (see Table 1 for the amount). To do this, measure the
next quantity of water, as listed in Table 1, in a 10 mL graduated cylinder (assume
that 1 g of water has a volume of 1 mL). Weigh the cylinder and water. Add the water
to the test tube. Weight the empty graduated cylinder. The difference between the two
masses is the mass of water added to the test tube. Calculate the total mass of water in
the test tube. Repeat the heating and cooling cycle, noting the temperature of
crystallization. Repeat the procedure of adding water, heating, and cooling for a total
of six measurements. If the temperature of the solution is approximately 20C and no
crystallization occurs, the test tube can be cooled by bringing a beaker of cold or ice
25

water up to the bottom of the test tube. Cool the mixture for no more than 5 seconds
each time, stirring, until the salt crystallizes.
Calculate the concentration (in g salt/100 g solvent) of the saturated solution at each
temperature.

26

Name(s)____________________________ Date _________________

SOLUBILITY OF A SALT IN WATER AT VARIOUS TEMPERATURES
Data:
salt used (write formula)
mass of salt used

____________
__________ g

Trial 1:
mass of 10-mL grad. cyl. + 1st addition of water
mass of 10-mL grad. cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature
Trial 2:
mass of 10-mL grad. cyl. + 2nd addition of water
mass of 10-mL grad. Cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature
Trial 3:
mass of 10-mL grad. cyl. + 3rd addition of water
mass of 10-mL grad. cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature
Trial 4:
mass of 10-mL grad. cyl. + 4th addition of water
mass of 10-mL grad. cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature
Trial 5:
mass of 10-mL grad. cyl. + 5th addition of water
mass of 10-mL grad. Cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature
Trial 6:
mass of 10-mL grad. cyl. + 6th addition of water
mass of 10-mL grad. Cylinder
mass of water added to test tube
mass of water present (total)
saturation temperature

27

__________ g
__________ g
__________ g
__________ g
__________C

__________ g
__________ g
__________ g
__________ g
_____ _____C

__________ g
__________ g
__________ g
__________ g
__________C
__________ g
__________ g
__________ g
__________ g
__________C
__________ g
__________ g
__________ g
__________ g
__________C

__________ g
__________ g
__________ g
__________ g
__________C

Summary and Calculations

salt used __________________
Trial

Mass of water
Present
g

Solution
Concentration
g salt/100 g H2O

Saturation
Temperature
C

Plot your data on graph paper or use Microsoft Excel. Draw a smooth curve to best fit
the points Plot the temperature (C) on the horizontal axis and the concentration (g
salt/100g water) on the vertical axis. Your graph should include title, axis labels, and
units of measure.
Also, plot the actual solubility of the salt on the same axes. How does your result
compare with the reference values?
Predict from your graph the solubility of the salt at 20C in g salt/100 g H20
Predict from your graph the solubility of the salt at 50C in g salt/100 g H20
List possible sources of error in determining the solubility of a salt in water at various
temperatures and discuss one of them as to how it would influence the results you
obtained.

28

EXPERIMENT 6
MOLECULAR GEOMETRIES OF COVALENT MOLECULES: LEWIS
STRUCTURES AND VSEPR THEORY
OBJECTIVE
To become familiar with Lewis structures, the principles of VSEPR theory, and the
three-dimensional structures of covalent molecules.
INTRODUCTION
Types of Bonding Interactions
Whenever atoms or ions are strongly attached to one another, we say that there is a
chemical bond between them. There are three types of chemical bonds: ionic,
covalent, and metallic. The term ionic bond refers to electrostatic forces that exist
between ions of opposite charge. A covalent bond results from the sharing of
electrons between two atoms. The more familiar examples of covalent bonding are
found among nonmetallic elements interacting with one another. This experiment
illustrates the geometric (three-dimensional) shapes of molecules and ions resulting
from covalent bonding among various numbers of elements, and one of the
consequences of geometric structures, polarity. Metallic bonds are found in metals
such as gold, iron and magnesium. In the metals, each atom is bonded to several
neighboring atoms and the bonding electrons are free to move throughout the metal.
Lewis Symbol
The electrons involved in chemical bonding are the valence electrons, those residing
in the incomplete outer shell of an atom. The Lewis symbol for an element consists of
the chemical abbreviation for the element plus a dot for each valence electron. The
dots are placed on the four sides of the atomic abbreviation. The number of valence
electrons of any representative element is the same as the group number of the
element in the periodic table. The Lewis structure of oxygen, for example, is shown
below
The Octet Rule
Atoms often gain, lose, or share electrons so as to achieve the same number of
electrons as the noble gas closest to them in the periodic table. According to the octet
rule then, atoms tend to gain, lose, or share electrons until they are surrounded by
eight valence electrons. There are many exceptions to the octet rule, but it provides a
useful framework for many important concepts of bonding.

Covalent Bonding
Lewis reasoned that atoms might acquire a noble-gas electron configuration by
sharing electrons with other atoms to form covalent bonds. The hydrogen molecule,
H2, provides the simplest possible example of a covalent bond. The attraction between
the nuclei and the electrons cause electron density to concentrate between the nuclei.
Lewis Structures
The formation of a covalent bond can be represented using Lewis symbols as shown
below for H2:

29

The formation of a bond between two F atoms to give a F2 molecule can be

represented in a similar way:

By sharing the bonding electron pair, each fluorine atom requires eight electrons (an
octet) in its valence shell. It thus achieves the noble-gas electron configuration of
neon. The structures shown here for H2 and F2 are called Lewis structures (or Lewis
electron-dot structures). In writing Lewis structures, we usually show each electron
pair shared between atoms as line, to emphasize it is a bond, and the unshared
electron pairs as dots. Writing them this way, the Lewis structures for H2 and F2, are
shown as follows:

Multiple Bonds
The sharing of a pair of electrons constitutes a single covalent bond, generally
referred to simply as a single bond. In many molecules, atoms attain complete octets
by sharing more than one pair of electrons between them. When two electron pairs are
shred, two lines (representing a double bond) are drawn. A triple bond corresponds to
the sharing of three pairs of electrons. Such multiple bonding is found in CO2 and N2.

Bond Polarity and Dipole Moments

A covalent bond between two different kinds of atoms is usually a polar bond. This is
because the two different atoms have different electronegativities and the electrons in
the bond are then not shared equally by the two bound atoms. This creates a bond
dipole moment, , which is a charge separation, Q, over a distance, r:

The bonding electrons have an increased attraction to the more electronegative atom,
thus creating an excess of electron density () near it and a deficiency of electron
density (+) near the less electronegative atom. We symbolize the bond dipole (a
vector) with an arrow and a cross,
, with the point
negative and the cross the positive end of the dipole. Thus, in the polar covalent
molecule HCl, because the chlorine is more electronegative than hydrogen, the
bond dipole is as illustrated below:

30

The bond dipole is a vector (it has a magnitude and direction), and the dipole
moments of polyatomic molecules are the vector sums of the individual bond dipoles.
Therefore, H2O has a dipole moment (a polar molecule) and CCl4 does not
(a nonpolar molecule).
VSEPR Theory
In covalent molecules, atoms are bonded together by sharing pairs of valence-shell
electrons. Electron pairs repel one another and try to stay out of each others way. The
best arrangement of a given number of electron pairs is the one that minimizes the
repulsions among them. This simple idea is the basis of valence-shell electron pair
repulsion theory, or the VSEPR model. Thus, as illustrated in Table 5.1, two electron
pairs are arranged linearly, three pairs are arranged in a trigonal planar fashion, four
are arranged tetrahedral, five are arranged in trigonal bipyramidal geometry, and six
are arranged octahedral. The shape of a molecule or ion can be related to these five
basic arrangements of electron pairs.
Predicting Molecular Geometries
When we draw Lewis structures, we encounter two types of valence-shell electron
pairs: bonding pairs, which are shared by atoms in bonds, and nonbonding pairs (or
lone pairs) such as in the Lewis structure for NH3. Because there are four electron
pairs around the N atom, the electron-pair repulsions will be minimized when the
electron pairs point toward the vertices of a tetrahedron (see Table 5.1). The
arrangement of electron pairs about the central atom of an AB molecule is called its
electron-pair geometry.
Table 6.1 Electron-Pair Geometries as a Function of the Number of Electron Pairs

31

However, when we use experiments to determine the structure of a molecule, we

locate atoms, not electron pairs. The molecular geometry of a molecule (or ion) is the
arrangement of atoms in space. We can predict the molecular geometry of a molecule
from its electron-pair geometry. In NH3, the three bonding pairs point toward three
vertices of a tetrahedron and the lone pair is located at a fourth vertex. The
arrangement of the atoms in NH3 is thus a trigonal pyramid, and the sequence of
steps to arrive at this prediction is illustrated in Figure 5.1. We see that the trigonalpyramidal molecular geometry of NH3 is a consequence of its tetrahedral electronpair geometry. When describing the shapes of molecules, we always give the
molecular geometry rather than the electron-pair geometry.

Figure 6.1
PRE-LABORATORY QUESTIONS
1. Write the Lewis dot structures for each of the following atoms: hydrogen, nitrogen,
silicon, sulfur, and bromine.
2. What information about a molecule does its Lewis dot structure provide?
3. What is the Octet Rule? Which element is the exception?
PROCEDURE
1. To predict molecular geometries with the VSEPR model:
a. Sketch the Lewis structure of the molecule or ion.
b. Count the total number of electron pairs around the central atom, and arrange them
in a way that minimizes electron-pair repulsions (Table 5.1).
c. Describe the molecular geometry in terms of the angular arrangement of the
bonding pairs, which corresponds with the arrangement of bound atoms.
d. A double or triple bond is counted as one bonding pair when predicting geometry.
2. Using an appropriate set of models, make molecular models of the compounds
listed below and completes the table.

32

Molecular
Formula

No. of
bond pairs

No. of lone
pairs
(around
central
atom)

Molecular
geometry

Bond
angle(s)

Dipole
moment
(yes or no)

BeCl2
BF3
SnCl2
CH4
NH3
H2O
PCl5
SF4
BrF3
XeF2
SF6
IF5
XeF4
3. Using an appropriate set of models, make molecular models of the compounds
listed in the sheet given to you by instructor and completes the table.
Molecule

Molecular No. of
Formula
bond
pairs

No. of
lone
pairs
(around
central
atom)

Phosphorous
trichloride
Ethylene
Ammonia
Ammonium
ion
Dihydrogen
sulfide
Carbon
tetraflouride
Carbonate ion
Carbon
disulfide
Formaldehyde

33

Molecular Bond
geometry angle(s)

Dipole
moment
(yes or
no)

EXPERIMENT 7
IDEAL GAS LAW
OBJECTIVE
Understand the application of ideal gas law
INTRODUCTION
Hydrogen peroxide (H2O2) is a common household item used to clean minor cuts. It
decomposes and forms a gas that is impossible to detect by smell. The bottle of H2O2
you purchase from any store contains % H2O2. The H2O2 slowly decomposes over
time to form water and oxygen gas. Oxygen gas is not easily detected when inhaled.
Ideal gas law, however, with the use of yeast as a catalyst can help in detecting the
amount of oxygen gas decomposed. Measuring the weight of any gas is difficult.
Laws such as the ideal gas law can be used to relate the number of moles to
measurements such as mass, volume, pressure, etc. Since H2O2 forms oxygen gas
when decomposed, ideal gas law can be used to check the H2O2% available in the
H2O2 commercial product. To calculate the percent H2O2, a small sample of the
commercial bottle H2O2 is taken to decompose through the use of a catalyst.

Yeast, containing the enzyme catalase, will get activated in warm water. The activated
yeast will then be added to a known amount of H2O2 in an Erlenmeyer flask. The flask
is quickly sealed so that the O2 gas formed is collected in the graduated cylinder.
After measuring the total volume of gas, the temperature and the atmospheric pressure
(will be given to you), the ideal gas law can then be utilized to calculate how many
moles of O2 gas is formed.

Percent yield H2O2 can now be found. To do this, divide (n), the actual number of
moles you calculated, by the theoretical moles of O2 multiplied by 100%.

This value can now be compared to the% H2O2 shown on the label of the commercial
bottle to see if any decomposition has occurred.
PRE-LABORATORY QUESTIONS
1.0 mol of H2 gas at 22 C and 748 Torr is trapped in an expandable/compressible
container. Use the ideal gas law to calculate the volume of the container?
Table 7.1 Chemicals and Supplies
Chemicals
Supplies
Yeast
Rubber band Flexible tubing (12 in.) 1 Pipettes 250 mL
Beaker 10 ml and 50 mL Graduated cylinders Stirring
2.5 mL of 3% H2O2
rod 600 mL Beaker

Erlenmeyer flask Thermometer Stopper with hole Warm

34

water* (will be provided) Burette clamp Rigid plastic

tubing (3 in.)
PROCEDURE
1. Set up your apparatus as in Fig 7.1. (Insert the smaller rigid tubing into one end of
the larger, flexible tubing. Insert the free end of the rigid tubing securely into the
rubber stopper hole).
2. Bend the free end of the flexible tubing into a U shape, and use the rubber band to
hold this shape in place. This will allow you to more easily insert this end of the
flexible tubing into the inverted graduated cylinder.
Note: Make sure the tubing is not pinched and the gas can flow freely through it.
3. Fill the 600 ml beaker with 400 ml tap water.
4. Fill the 50 ml graduated cylinder with tap water slightly over the 50 ml mark.
5. Measure the temperature of the water in the 600 ml beaker, and record it in the data
section. Hint: The lab pressure is 1.00 atm.
6. Mix 100 ml of warm water (45C) with 8.0 grams of yeast in 250 ml beaker. This
will activate the yeast from the dormant (dry) state. Be sure to mix well with the
stirring rod until the yeast is completely dissolved.
7. Use a 10 ml graduated cylinder to measure 2.50 ml of H2O2. Pour the measured
H2O2 into the Erlenmeyer flask, and place the stopper with stopper tube over the top.
Then rinse your cylinder and put it aside.
8. Cover the opening of the graduated cylinder with three or four of your fingers and
quickly turn it upside down into the 600 ml beaker already containing the 400 ml of
water. Do not remove your fingers from the opening until the graduated cylinder is
fully submerged under the water. If the amount of trapped air exceeds 10 ml, refill the
cylinder and try again.
9. Insert the U shaped side of the flexible tubing into the beaker, and carefully snake it
into the submerged opening of the graduated cylinder. You want as little air as
possible to be in the graduated cylinder.
10. Attach the burette clamp to the stand to secure the graduated cylinder to the
burette clamp.
11. With the cylinder vertical, record the volume of air inside (the line at which the
water reaches in the cylinder) in the data section.
12. Using the pipette, measure out 2.50 ml of yeast solution into the rinsed 10 ml
graduated cylinder.
Note: Do not pour the yeast solution into the Erlenmeyer flask immediately.
13. Prepare to place the stopper (still connected to the hose) on the Erlenmeyer flask.
14. Quickly pour the 2.5 ml of yeast solution into the Erlenmeyer flask. Immediately
place the stopper securely in the opening of the Erlenmeyer flask by twisting it down
into the flask gently.
15. Swirl the Erlenmeyer flask to mix the two solutions together.
16. You will begin to see bubbles coming up into the 50 ml graduated cylinder. Hint:
if gas bubbles are not immediately visible, make sure the stopper is on tight enough
and the tubing is not leaking. You will need to start over after correcting any problem.
17. Continue to swirl the Erlenmeyer flask and let the reaction run until no more
bubbles form to ensure the reaction has gone to completion. This should take
approximately 3-6 min. Hint: Catalase enzyme works best around the temperature of

35

the human body (37C). You can speed the reaction up by covering the Erlenmeyer
flask with your hands.
18. Record the time when the reaction is finished in table 2 of the data section, along
with the final volume of air. Remember to read it at eye-level and measure from the
bottom of the meniscus.
19. Pour all other liquids down the drain and clean the lab-wares.
20. Take apart your apparatus when you finish your experiment

Figure 7.1
Table 7.2: Collecting data

CALCULATIONS
1. Convert the temperature of the water from C to Kelvin (K). Use the equation
K= C + 273.
2. Convert the volume of oxygen from ml to liter (L).
3. Rearrange the ideal gas law to solve for n. and be sure the units cancel so that you
end up with only the moles of O2 left which is going to represent the actual number of
moles of O2.
4. Calculate the theoretical number of moles of O2.
Note: the density of H2O2 is 1.02 g/mL.
5. Find the %yield of H2O2 using the equation below and compare it to the % H2O2
shown on the label of the commercial bottle to see if any decomposition has occurred

CONCLUSION
Compare the calculated % yield of hydrogen peroxide with the commercial bottle of H2O2
used.

36

EXPERIMENT 8
PROPERTIES OF ALCOHOLS: STRUCTURE, REACTIONS AND
IDENTIFICATION OF ALCOHOLS
PURPOSE
a) Examine molecular models and observe some physical and chemical properties of
selected alcohols.
b) Relate the observed properties to the molecular structure. Identify an unknown
alcohol.
c) To learn some common properties of alcohols
d) To distinguish phenols from the three types of alcohols by chemical tests.

CHEMICALS
MATERIALS
Ethyl alcohol (ethanol)
small test tubes (8 to 10)
Isopropyl alcohol (2-propanol)
stirring rod
t-butyl alcohol (2-methyl-2-propanol)
hot plate
cyclohexanol beakers (50, 400 mL)
1-propanol (n-propanol)
test tube holder
1-butanol
test tube rack
2-butanol
unknown alcohols
acetic anhydride
glacial acetic acid
conc. H2SO4
diluteNaOH
Lucas reagent (ZnCl2 in concentrated HCl)
Chromic acid reagent - 2% K2Cr2O7 in H2SO4 (oxidant)
Sodium metal
Phenolphthalein indicator
INTRODUCTION
Alcohols are organic compounds containing an -OH functional group bonded to a
carbon atom. There are three classes (types) of alcohols: primary, secondary, and
tertiary as shown below.
Primary alcohol: RCH2OH the R, an alkyl group, and the OH are attached to a
primary carbon atom, a carbon bonded to one other carbon atom (highlighted).

Secondary alcohol: R2CHOH, the 2 R alkyl groups, and the -OH are attached to a
secondary carbon atom, a carbon attached to two other carbon atoms from the
2 R(CH3-),

37

Tertiary alcohol: R3COH the 3 R alkyl groups, and the OH are attached to a
tertiary carbon atom (highlighted), a carbon attached to three other carbon atoms from
the 3 R (CH3-)

The International Union of Pure and Applied Chemistry (IUPAC) method of

nomenclature for alcohols use the ending ol. Change the e ending of an alkane to ol
(i.e methane to methanol ethane to ethanol). R = represents any alkyl group
Physical Properties
Molecular State- Straight-chain alcohols with up to 12 carbon atoms are liquids.
Solubility- Alcohols with a small organic part such as methanol or ethanol are much
like water, thus miscible with water. Alcohols with a larger organic radical are more
like alkanes and less like water. Alcohols with more than two OH groups are more
water soluble than similar alcohols with only one OH group. In general each OH
group can solubilize four to five carbons
Melting (Fusion), Boiling points and Density- Straight-chain alcohols that have up
to 12 carbons have boiling points that are considerably higher than the related alkanes,
Alcohols with two or more OH groups have higher boiling points. Because the
structural similarities between alcohols and water, their physical properties are also
similar. Hydrogen bonding has a great influence on the physical properties of
alcohols.
Alcohols with short carbon chains are quite soluble in water. Their solubility is due
to intermolecular hydrogen bonding with water molecules, as shown in Figure 1(b).
However, the water solubility of alcohols begins to decrease as the length of the
carbon chain increases. As the number of carbon atoms increases, the non-polarity of
the larger hydrocarbon chain offsets the polarity of the OH group. Alcohols with
longer carbon chains are insoluble. Because they are less dense than water, insoluble
alcohols will form a layer on top of the water surface.

38

Figure 8. 1. Hydrogen bonding between (a) alcohol molecules, and (b) alcohol and
water molecules
Also, considering their molecular masses as compared to alkanes, alcohols have
relatively high boiling points. Individual alcohol molecules are attracted to each
other by hydrogen bonds. A higher temperature is necessary for these molecules to
have sufficient energy to overcome these attractions. When enough energy breaks the
hydrogen bonds, the alcohol converts from a liquid alcohol to a gaseous alcohol.
Viscosity refers to the resistance to flow. As the degree of intermolecular hydrogen
bonding increases, the more viscous the liquid becomes. We commonly call viscous
liquids thick.
Many alcohols have characteristic odors that are readily detected. Particle size and
hydrogen bonding both influence the ability of particles to escape from the liquid
surface into the air. Greater size and greater intermolecular forces decrease the
potential for alcohols to escape the liquid surface.
Main Uses- Some of the most common uses we have for alcohols are in medical
clinics or at home for disinfecting things. Ethyl alcohol is classified for medical
purposes as a central nervous system depressant this is the alcohol that people like
to drink, and it is obtained by the fermentation of fruits. Another use that isnt as
popular is to synthesize other substances in laboratories.
Chemical Properties of Alcohols:
Alcohols are neutral compounds; the hydroxyl group does not ionize. However, the
alcohol functional group is chemically reactive in other ways. Alcohols can be
dehydrated. Depending upon the reaction conditions, loss of a water molecule forms
either an ether or an alkene.
Oxidation of alcohols by strong oxidants such as K2Cr2O7 in H2SO4 is possible, but
differs depending on the degree of alcohol. Examples a, b, and c below show how a
primary, secondary, and tertiary alcohol respectively respond to treatment of oxidants.
If a reaction has occurred using K2Cr2O7 in H2SO4, there is a color change from
orange to green.

39

In this experiment, an acidic sodium dichromate solution, which is orange in color

and contains Cr6+, will be used to oxidize alcohols. As the alcohol is oxidized, the
Cr6+ is reduced to Cr3+, which turns the solution a blue-to-green color. The appearance
of this blue-to-green color within one minute is considered a positive test for a
primary or a secondary alcohol.
Lucas Test: This test is for low molecular weight alcohols and it distinguishes the
rates of reaction of alcohols with the Lucas reagent (HCl and ZnCl2). Positive
indicator of the reaction is the formation of a water insoluble alkyl chloride as
cloudiness or a precipitate. The formation of an alkyl chloride with tertiary alcohol is
very rapid, followed by the secondary alcohol that may take from 5 to 20 minutes to
form visible cloudiness. Primary alcohols do not react with Lucas reagent or it may
show very little result in a very long time. The chemical reaction involves replacing

40

the OH group of the alcohol with a chloride ion from hydrochloric acid (HCl),
forming an alkyl chloride, as shown in the following equation.

Zinc chloride (ZnCl2) is a catalyst for this reaction, which is called the Lucas test. The
resultant alkyl chloride is insoluble in water and separates from the Lucas reagent
(ZnCl2 in concentrated HCl), forming a cloudy mixture. Alcohols react at different
rates, depending upon their structure. Tertiary alcohols form a cloudy mixture within
30 seconds at room temperature. Secondary alcohols react within 13 minutes,
usually with slight heating. Primary alcohols require more than an hour to react.
Esterification: Esters are derivatives of organic acids. They can be prepared by the
reaction of alcohols with carboxylic acids in the presence of a catalytic amount of
mineral acid. Esters usually have pleasant, fruitlike odors and are responsible for
flavors and fragrances of many fruits and flowers.
Note: Record all your observations on your Data and Observations sheet. Dispose of
your reaction mixtures according to your laboratory instructors directions.
Safety Note
Caution: Wear departmentally approved safety goggles when doing this experiment.
All chemicals are potentially harmful. Prevent contact with your eyes, skin, and

41

clothing. Avoid ingesting any of the reagents. If you spill any reagents, immediately
notify your laboratory instructor.
All the alcohols used are toxic, except glycerol. All the alcohols are flammable, except
glycerol and ethylene glycol. Do not perform the experiment near an open flame.
Chromic acid reagent is toxic, corrosive, oxidant, and contains a suspected
carcinogen. Acetone is flammable and irritating. Do not use acetone near an open
flame.
Lucas reagent (ZnCl2 in concentrated HCl) is toxic and corrosive.
PROCEDURE
Part I Reaction with sodium
Under the hood place a small piece of sodium metal in to a 50 mL beaker of half filled
with water. Observe the reaction and after completion of the reaction, add 1 or 2 drops
of phenolphthalein indicator to the solution in the beaker. Write a balance equation for
the reaction of sodium and water. Repeat the reaction of 2.0 mL alcohol with small
piece of sodium metal in a large dry test tube. Note the reactivity of sodium metal
with alcohol in compare (less or more reactive) to water. Test the resulting solution
with phenolphthalein. Write the balance equations for reactions of sodium with
ethanol and 1-butanol, phenol, and unknown.
Part II Solubility in water
Place 2.0 mL of water in a small test tube, drop wise add ethanol and shake the
mixture. Count the number of drops until the alcohol is no longer soluble in water, but
do not use more than 10 drops. Repeat the same procedure using 2-propanol, 1butanol, cyclohexanol, phenol, and unknown. Record your results as very soluble (for
6-10 drops), soluble (for 2-5 drops), and insoluble (1 drop).
Part III. Lucas Test
In a small test tube place 2.0 mL Lucas reagent, and add 4-5 drops of alcohol, shake
the mixture well and observe the time required for the mixture to become cloudy or to
form two different phases (layers). Try this test with 1-butanol, 2-butanol, 2-methyl-2propanol (t-butyl alcohol), phenol, and unknown. Based on your results of the Lucas
test, determine the type of your unknown alcohols (1o, 2o, or 3o)
Part IV. Jones Reagent (Chromic acid test)
In a small test tube, place about 1.0 mL acetone, 1.0 mL alcohol, and 2 3 drops of
the Jones reagent. Observer the color change, clear, orange (formation of Cr +6 as
CrO3), or blue-green (formation of Cr 3+). Try this test with 1-butanol, 2-butanol, 2methyl-2-propanol, phenol, and unknown. Based on your results of the Chromic acid
test determine the type of your unknown alcohol (1o, 2o, or 3o).
Part V. Esterification
a) In a small test tube, mix ethanol (4-5 drops) and acetic acid (4-5 drops). Add
one drop of concentrated sulfuric acid, warm the mixture in a hot water bath
for about 5 minutes and then add 2.0 mL of cold water. Note the odor and
write a complete equation for the reaction of ethanol and acetic acid.
b) In a small test tube, mix 1-butanol (4-5 drops) and acetic anhydride (4-5
drops). Stir well, and warm the solution in hot water bath. Add 2.0 mL of cold

42

water and make mixture slightly basic by adding 4-5 drops dilute NaOH. Note
the odor and write a complete equation for the reaction of 1-butanol and acetic
anhydride.

43

EXPERIMENT 8
PROPERTIES OF ALCOHOLS
REPORT FORM Name _______________________________
Instructor ___________________________
Date ________________________________
Part I Reaction with sodium
Compound
Water
Ethanol
1 -Butanol
Phenol
Unknown # _____

Observation

Part II Solubility in water

Alcohol
Ethanol
2- propanol
1- Butanol
Cyclohexanol
Phenol
Unknown # ______

Observation

Part III. Lucas Test

Alcohol
1-butanol
2-butanol
t-butyl alcohol
2-methyl-2-propanol
Phenol
Unknown # _____

Observation

Jones Reagent (Oxidation Using Chromic Acid)

Alcohol
1-butanol
2-butanol
t-butyl alcohol
(2-methyl-2-propanol)
Phenol
Unknown # _____

Observation

44

Esterification Ester Formation

a) Ethanol + acetic acid Odor __________
Reaction: ___________________________
b) 1-Butanol + acetic anhydride Odor __________
Reaction: _____________________________________
UNKNOWN IDENTIFICATIONS (1o, 2o, or 3o)
Unknown Number ______ Identification _______
PRE-LABORATORY QUESTIONS
1. What are the specific hazards associated with the alcohols used in this
experiment? What are the specific hazards associated with the chromic acid
reagent?
2. Consider the alcohol hexyl alcohol (1-hexanol), C6H14O. Draw both a
structural formula and a condensed structural formula for 1-hexanol. Identify
1-hexanol as a primary, secondary, or tertiary alcohol
3. What would you expect to observe if you performed the chromic acid test on a
sample of 1-hexanol?
4. What would you expect to observe if you performed the Lucas test on a
sample of 1-hexanol?
5. Aqueous solutions of isopropyl alcohol are commonly sold as rubbing alcohol.
The boiling point of isopropyl alcohol is 82.4 C. It evaporates readily from
the surface of the skin. Ethylene glycol (CH2OHCH2OH) is sold as
antifreeze/antiboil. The boiling point of ethylene glycol is 198 C. The
molecular masses of isopropyl alcohol and ethylene glycol are similar. Provide
an explanation for the observed difference in their boiling points.
6. Explain any differences observed between the solubility, viscosity, and the
odor of ethyl alcohol and glycerol (CH2OHCHOHCH2OH)
7. Chromic acid oxidation is the basis of the Breathalyzer Test used by many
police departments to detect ethyl alcohol in the breath of people suspected of
driving under the influence. The amount of the green product is proportional
to the amount of ethyl alcohol in the breath. Write structural formulas for the
two oxidation products formed from ethyl alcohol. Name the oxidation
products
8. If you exercise strenuously without sufficient oxygen, lactic acid accumulates
and contributes to muscle fatigue and soreness. When oxygen is later
available, lactic acid must be oxidized to pyruvic acid. The structure of lactic
acid is shown below.

45

(a) Circle the alcohol functional group. Classify the alcohol as primary, secondary, or
tertiary.
(b) Predict the solubility and chromic acid test results for lactic acid.
(c) Complete the reaction equation above. Draw the formula of the reaction product,
pyruvic acid.
9. Containers of antifreeze contain such warnings as Dispose of ethylene glycol
properly and Keep out
of the reach of children and animals. Considering the chemical reactivity of alcohols,
suggest a specific reason for these types of warnings.

46

EXPERIMENT 9
CARBOXYLIC ACIDS REACTIONS AND DERIVATIVES
MATERIALS
Medium test tubes (6) Test tube rack Beakers (50, 150, 400 mL)
Ice Hot plate Graduated cylinders (10, 25-mL)
CHEMICALS
Benzoic acid 10% NaOH Sodium acetate Red/Blue litmus papers pH papers
Methanol conc. H2SO4 Acetamide 10% H2SO4 Salicylic acid, Butanol Acetyl chloride
PURPOSE
Study the Carboxylic acids and their derivatives with one or more carbonyl groups.
Reactions such as formation and hydrolysis of carboxylic salts and esterification. This
experiment will illustrate some of the more important reactions of carboxylic acids
and their derivatives.
INTRODUCTION
Carboxylic acids contain one or more carboxyl functional groups (-COOH). The
IUPAC nomenclature drops the ( -e ) of the suffix of the Alkane name and adds ( -oic
acid), review the names of the first ten alkanes and convert these names to the
corresponding carboxylic acid. The carboxyl functional group is polar, both at the
carbonyl part and at the hydroxyl part because of the difference in electronegativity
value of carbon - oxygen, and oxygen - hydrogen. Thus carboxylic acids form
hydrogen bond with themselves and any other appropriate polar molecule, and this
structure will influence their physical properties and their chemical properties as we
have seen in other cases. Note that if the number of total carbons is more than one, for
example six, then five of the carbons are hydrocarbons and non-polar. The resulting
molecule then has a hydrophilic part (the carboxyl group) and a hydrophobic part
(the other five carbons with their associated hydrogen atoms). One area will be
soluble in water and the other not soluble in water. Note also that the hydrocarbon
part has much reduced carbon. The carboxyl group differs from a hydroxyl group in
having a delocalized negative charge and this results in resonance stability. Note this
means that either oxygen (carbonyl or hydroxyl) can double bond when proton is
removed from hydroxyl.
Carboxylic acids are an important class of organic compounds. Other important
classes of compounds called acid derivatives are related to acids but differ from them
in that the hydroxyl portion of the carboxyl function is replaced by other groups.
Among these acid derivatives are the acyl halides, anhydrides, esters, and amides.

47

Review carboxylic acid derivatives nomenclature

Acyl Halides: The acyl group is named first, followed by the halogen name as a
separate word. CH3CH2COCl is propanoyl chloride (or propionyl chloride).
Acid anhydrides: The name of the related acid(s) is used first, followed by the
separate word "anhydride". (CH3(CH2)2CO)2O is butanoic anhydride
CH3COOCOCH2CH3 is ethanoic propanoic anhydride (or acetic propionic
anhydride).
Esters: The alkyl group is named first, followed by a derived name for the acyl
group, the oic or ic suffix in the acid name is replaced by ate.
CH3(CH2)2CO2C2H5 is ethyl butanoate (or ethyl butyrate)( ethylpropyl ester).
Cyclic esters are called lactones. A Greek letter identifies the location of the alkyl
oxygen relative to the carboxyl carbonyl group.

Amides: The name of the related acid is used first and the oic acid or ic acid suffix is
replaced by amide (only for 1-amides). CH3CONH2 is ethanamide (or acetamide)(1o
amide) 2 & 3-amides have alkyl substituents on the nitrogen atom. These are
designated by "N-alkyl" term(s) at the beginning of the name. CH3(CH2)2CONHC2H5
is N-ethylbutanamide; (2o aminde) HCON(CH3)2 is N,N-dimethylmethanamide (or
N,N- dimethylformamide) (3o amide). Cyclic amides are called lactams. A Greek
letter identifies the location of the nitrogen on the alkyl chain relative to the carboxyl
carbonyl group.

PART A. Carboxylic Acid Salts

I. Salt Formation
Carboxylic acids may be neutralized by strong base to give salts. Because salts are
ionic and usually water soluble, acids that are only slightly soluble in water can
extracted by aqueous base from a solution in an organic solvent.

48

II. Salt Hydrolysis

Because carboxylic acids are weak acids partially dissociated in aqueous solution,
their salt solutions are alkaline. In water, a carboxylic acid salt hydrolyzes to the
undissociated acid and hydroxide ion.

PART B. Esters :
Esters can be prepared by the reaction of alcohols with carboxylic acids or their
derivatives.
The acid catalyzed reaction of an alcohol with a carboxylic acid is most commonly
used for such preparations. The acyl halide ion is a good leaving group making acyl
halides very reactive toward nucleophilic acyl substitution. Acid halides ( or acyl
halides) are highly reactive that they are not found in nature, since they even react
with water. For small- scale preparations, however, the reaction of an acyl halide with
an alcohol is often faster and simpler.

49

PART C. Amides: Hydrolysis of an Amide

Three classes of amides are known:

Of the various acid derivatives studied here, amides are the least reactive toward
nucleophilic attack, because the unshared electron pair on the nitrogen is delocalized
to the carbonyl carbon through resonance. Thus, unlike most acyl halides or
anhydrides, amides must be heated to boiling with aqueous acid or base in order to
hydrolyze them. For a primary amide, the product will be ammonium ion and the acid
(for acidic hydrolysis) or ammonia and carboxylate ion (for alkaline hydrolysis). The
reaction mechanisms are similar to those for the hydrolysis of other acid derivatives.
In this experiment you will hydrolyze acetamide under alkaline and acidic conditions.

50

Example:

Safety Note
Caution:
1. Acetic anhydride is irritating in the liquid or vapor state. Avoid contact with skin
and eyes.
2. When handling concentrated sulfuric or phosphoric acid be careful to avoid
contact with skin and clothing. Wear disposable gloves.
PROCEDURE
Part A- Carboxylic Acid Salts.
I. Salt Formation
In each of two test tubes, place 0.1 g of benzoic acid. To one tube, add 3 ml of cold
water, to the other, add 3 ml of 10% sodium hydroxide solution. Shake both tubes,
observe, record the result, and write a complete reaction.
II. Salt Hydrolysis
This hydrolysis can be demonstrated by testing the salt solution with litmus paper.
Dissolve approximately 0.2 g of sodium acetate in 5 ml of distilled water. Test the
resulting solution with litmus paper, and note the results. Wash the aqueous solution
down the sink with plenty of water. Record the result, and write a complete reaction.
PART B. Esters - Preparation of Methyl Salicylate (Oil of Wintergreen)
I. Dissolve 0.5 g of salicylic acid in 5 ml of methanol in a small beaker. Cautiously,
with constant stirring,

51

2. Add 10 drops of concentrated sulfuric acid to the mixture. Heat the mixture on the
steam bath for 10 min, then pour it over about 10 g of ice in a small beaker.
3. Stir well and cautiously observe the odor of the product by gently wafting the
vapors toward your nose.
4. Record the result, and write a complete reaction.
5. Add drop-by-drop 1 ml (~ 20 drops) of acetyl chloride to 1 ml of butanol. Allow to
stand for about 2 minutes and then pour carefully into 5 ml of water (acetyl chloride
reacts vigorously with water).
Note: the odor of solution by wafting the smell toward your nose. Remove a little of
the insoluble layer with a dropper and test its solubility in 5% NaOH solution.
PART C. Amides: Hydrolysis of an Amide
Add 0.5 g of acetamide to 5 ml of 10% sodium hydroxide solution in a test tube, and
gently warm the solution, and heat the mixture to boiling. Note the odor of the
evolved gas by gently wafting its vapors toward your nose. Test the gas by holding a
piece of moist red litmus paper in the mouth of the tube. Repeat the experiment with
0.5 g of acetamide and 5 ml of 10% sulfuric acid. Record the result, and write a
complete reaction(s).

52

EXPERIMENT 9
Name _______________________________
Instructor ___________________________
Date _______________
Part A- Carboxylic Acid Salts.
I. Salt Formation
Compound Solvent Solubility(observation)
Benzoic acid Cold water
Benzoic acid 10% NaOH
Reaction: _____________________________________________________________
II. Salt Hydrolysis
Sodium acetate solution changed the color of litmus from ________ to _________ .
Reaction: _____________________________________________________________
PART B. Esters - Preparation of Methyl Salicylate (Oil of Wintergreen)
I.
Describe
the
odor
of
the
product. ___________________________________________________
Reaction: _____________________________________________________________
II.
Describe
the
odor
of
the
product. _________________________________________________________
Reaction: __________________________________________________________
PART C. Amides - Hydrolysis of an Amide
a. Odor of the gas and its effect on
____________________________

litmus

for

basic

hydrolysis:

Reaction: _______________________________________________________
b. Odor of the gas and its effect on litmus for acidic hydrolysis:
_________________________________
Reaction:_____________________________________________________________
___________________
PRE-LABORATORY QUESTIONS
1. Write a complete reaction of succinic acid and acetic anhydride.
2. Write an equation that accounts for the solubility of propanoic acid in aqueous
base.
3. Write equations that describe the reaction mechanism for acid hydrolysis of each of
the following compounds.
a) Acetyl Chloride
b) Acetic anhydride
4. Explain why acetyl chloride is hydrolyzed faster than benzoyl chloride.

53

5. Write an equation for the reaction of n-butyl alcohol with acetyl chloride. What gas
evolved?
6. Write an equation for the reaction of aniline with acetic anhydride.
7. Give structure for the following compounds;
a) Pentanolactam
b) b) pentanolactone
8. Name two dicarboxylic acids and draw their structures
9.What is the difference between dehydration and hydrolysis? Give examples.
10. Define esterification and give an example.

54

References
1. Rose, A. K., Elya, S. M., Tee, H. D., Chemistry II Laboratory Manual, 2012.
2. Mariam, M., General Chemistry I Laboratory Manual, 2013.
3. http://chemistry.about.com/od/healthsafety/a/aa080104a.htm
4. http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Ap
pendix/ClassificationTests/
5. http://orgchem.colorado.edu/Technique/Procedures/Extraction/Extraction.html
6. http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Ap
pendix/ClassificationTests/aldehyde_ketone.html

55