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EXERCISE 9

ACYL COMPOUNDS: SOAPS AND DETERGENTS

I.

INTRODUCTION
A. Acyl Compounds

Acyl compounds are of the type

,where G is a halogen

bonded to the carbonyl group through oxygen or nitrogen. The most


widely distributed acyl compunds ar the carboxylic acids. Carboxylic acids
are the most important of the acidic organic compounds. They contain the
carboxyl group as their functional hroup:
O

R = alkyl or aryl
R

OH

In the carboxyl group, the hydroxyl group is directly attached to the


carbonyl group which allows the resonance stabilization of the conjugate
base formed upon release of a proton:
O

+
R

:Base

+
R

OH

H-Base

Thus, carboxylic acids have a greater tendency to release a proton


than other organic compound types.
O

Usually, carboxylic acid functional derivatives contain the acyl group


R

The following types are functional derivatives of carboxylic acids:


O

OH
R

acid halide

acid anhydride

ester

H3C

NH2

amide

O
H

H 3C

H3C

R1

substituted amides
Nitriles, R - CN, though not acyl compounds, are considered as
carboxylic acid functional derivatives because they are readily hydrolyzed
to carboxylic acids.
Nucleophilic addition to the carbonyl group is less likely in acyl
compounds than in aldehydes and ketones. The characteristic reaction of
acyl compounds is nucleophilic acyl substitution:

+
R1

:Nu

H3C

G
Nu

+ G-

H3C
Nu

Through this reaction, carboxylic acids may be converted to the


functional derivatives and in turn, the functional derivatives may be
converted to carboxylic acids.
The acyl compounds differ in their reactivities toward nucleophilic
acyl substitution and this is evident from their hydrolysis reactions. The
more reactive compounds are hydrolyzed by water alone. The less
reactive ones either require a strong nucleophile as the hydroxide ion or
an acid catalyst to enhance the electron deficiency of the carbonyl carbon,
making it more attractive to a nucleophile. Alcohols, phenols, ammonia
and amines react with acyl compounds in much the same way as water
does.

B. Soaps and Detergents


Esters of long chain carboxylic acids and the trihydric alcohol,
glycerol, are known as triacylglycerols or triglycerides. The carboxylic
acids attached to glycerol may be identical (simple triglycerides), or
different (mixed triglyceride).

O
H2C

OH

H2 C

C R
O

HC

OH

HC

C R1
O

H2C

OH

H2 C

glycerol

R2

triacylglycerol

Triacylglycerols undergo the same reactions as the low molecular


mass esters; hydrolysis in a basic medium yields long chain
carboxylate salts and glycerol. This reaction is called saponification;
the salts produced are called soaps.
Soap produced from
triacylglycrols is a mixture of long chain carboxylate salts.

O
H2 C

C R
O

HC
H2 C

O
O

C R1
O

C R2

H2C

OH

HC

OH

3NaOH

+
R

H2C

O
-

O Na R1

O Na R2

O Na

OH

soaps

Detergents on the other hand, are also amphiphatic and are


generally characterized by the presence of a sulfate group. They are
usually derived from C12 to C18 alcohols:

CH3(CH2)10CH2OH

H3C(H 2C) 10 H2C

S
O

lauryl alcohol

II.

lauryl hydrogen sulfate

O
OH

H3C(H 2C) 10 H2C

S
O

sodium lauryl sulfate


DETERGENT

OBJECTIVES
1. To observe the general properties of carboxylic acids.
2. To compare the acidity of carboxylic acids and phenols.
3. To verify experimentally the interconversion among acyl compounds.

O Na

4. To become familiar with the physical and chemical properties of fats


and oils and to understand the chemical basis of these properties.
5. To learn how to prepare soap.
6. To compare the properties of soap and synthetic detergents.

III.

PROCEDURE

A. Solubility and acidity of carboxylic acids


1. Water silubility
*Perform this test with acetic acid, benzoic acid, and sodium benzoate
a.
b.
c.
d.

Place 2 mL water in a test tube.


Add a small amount of the sample (6 drops or a small piece)
Shake to mix.
Examine the mixture. Test with blue litmus paper

2. Relative acidities of carboxylic acids and phenols


*Perform using benzoic acid and phenol
a.
b.
c.
d.
e.

Place 2 mL water in a test tube


Add 6 drops of the sample
Add 10 drops of 10% NaOH
Examine the mixture
Repeat using 10% NaHCO3 instead of NaOH

B. Hydrolysis of acyl compounds


Perform this test with acetyl chloride, acetic anhydride, ethyl benzoate and
benzamide as samples
CAUTION: ACETYL CHLORIDE AND ACETIC ANHYDRIDE MUST BE
HANDLED IN THE FUME HOOD
1.
2.
3.
4.

Place 6 drops or a spatula tip of sample in a test tube


Add 3 mL water carefully
Observe for any sign of reaction (e.g. heat evolved, bubbles, etc.)
If no change is seen, heat the test tube for 2 minutes without boiling in
a hot water bath
5. Cool the mixture
6. Test with blue litmus paper
C. Saponification of coconut oil
1. Place 10 mL ethanol in a 400 mL beaker
2. Add 15 mL 6 M NaOH
3. Add 15 mL coconut oil; mix by swirling
4. Add boiling chips and cover the beaker with a watch glass

5. Heat the mixture while swirling over a small flame. Continue for about
15 minutes or until the mixture is viscous
6. Cool the mixture
7. Add 50 mL saturated NaCl solution while stirring
8. Suction filter the product
9. Wash the soap twice with 15 mL ice-cold distilled water
10. Allow to dry
D. Comparison of soaps and detergents
Dissolve one spatula tip of soap sample in 30 mL of warm distilled water. Do
the same with a sample of detergent. Use mixtures formed for the following
tests.
1. Hydrolysis
Test the mixture with red and blue litmus paper
2. Reaction with acid
a. Place 5 mL of the sample in a test tube
b. Add 10 mL 0.5 M HCl
c. Shake to mix. Observe
3. Reaction with soft and hard water
a. Place 5 mL of 0.02 M NaCl (soft water) in a test tube
b. Add 15 drops of the sample
c. Repeat with 0.02 M CaCl2 (hard water)
4. Emulsifying action
a. Place 8 drops of kerosene in a test tube
b. Add 5 mL sample
c. Shake the tube vigorously for three minutes
d. Allow to stand for 5 minutes. Run water blank.

IV.

QUESTIONS
1. Explain the difference in the solubility of benzoic acid and sodium
benzoate in water. Which of the two would you predict to be more
soluble in CHCl3? Explain.
2. Based on the results in Part A.2, what can be said about the relative
acidities of phenols and carboxylic acids? Arrange the following
compound types in order of increasing acidity: carboxylic acid, alcohol,
phenol and water.
3. Based on the results in Part B, arrange the following compound types
in the order of decreasing hydrolysis rate: acid halides, acid

anhydrides, esters, and amides. Give the theoretical explanations for


the observed differences in reaction rates.
4. Is the soap water mixture a true solution? Cite examples to support
your answer.
5. What is a colloidal mixture? How does a colloidal mixture arise when
soap is mixed with water?
6. On the basis of the litmus test, are the soap-water and detergent-water
mixtures acidic, basic or neutral? Explain the difference, if any in the
reactions of the soap-water and detergent-water mixtures to litmus
paper.
7. Which would you predict to have a greater emulsifying power in hard
water, soaps or synthetic detergent? Explain.
8. Explain the cleaning property of soaps and detergents based on your
observations of their emulsifying action.