DEPARTMENT OF CHEMICAL ENGINEERING

College of Enginering
Bicol University
Legazpi City

Organic Chemistry 2

Laboratory Plan

ACYL COMPOUNDS:SOAPS AND

DETERGENTS

Prepared by:
Joyce Ann Antonio
Joanna Marie C. Apuya
Charles Matthew Atos
Renzo Bagacina
Quennie Marie Banares

BS Chemical Engineering III

Submitted to:
Engr. Marco Angelo Dejucos
Instructor
I. INTRODUCTION

A. Acyl Compounds O

Acyl compounds are of the type R G

,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 O O
+ :Base + H-Base
- R O
R OH R O

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 O O OH O
R
R X R O R R O H3C NH2

acid halide acid anhydride ester amide

O O

H R1
H3C N H3C N

R R

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:

-
O O O

+ :Nu H3C G H3C + G-

R1 G Nu
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 H2C O C R
O
HC OH HC O C R1
O
H2C OH H2C O C R2

glycerol 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
H2C O C R
H2C OH
O O O
O
+ 3NaOH HC OH +
HC O C R1 - - -
O R O Na R1 O Na R2 O Na
H2C O C R2 H2C 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:

O O
- +
CH3(CH2)10CH2OH H3C(H 2C) 10H2C O S OH H3C(H 2C) 10H2C O S O Na

O O

lauryl alcohol lauryl hydrogen sulfate sodium lauryl sulfate

DETERGENT
II. 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.
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 compare the properties of soap and synthetic detergents.

III. MATERIALS AND REAGENTS

Materials:
Quantity Specification Descriptions
5 - Medicine dropper
18 medium Test tubes
2 - Test tube holder
 2 - Test tube rack
1 - Test tube brush
1, 3 1mL, 5mL Pipette
3 - Aspirator
1, 2, 10 250 mL, 100 mL, 50 mL Beaker
3 70 mm Watch glass
1 - Stirring rod
50 mL Volumetric Flask
1 250 mL Volumetric Flask
2 each Red and blue litmus paper
1 - Analytical balance
1 - Iron ring
1 - Iron stand
1 - Iron clamp
1 - Wire gauze
1 - Burner
2 - Filter paper
1 - Hot plate

Reagents:
Quantity Specifications Descriptions
2mL Liquid Acetic acid
3mL Liquid Benzoic acid
1g Solid Sodium benzoate
6 drops Liquid Phenol
5.5 g Solid NaOH
5.5145 g Solid 3
- - Acetyl chloride
- - Acetic anhydride
- - Ethyl benzoate
- - Benzamide
0.0584 g Solid NaCl
0.11098 g Solid 2
1.035 mL Liquid HCl
1 mL Liquid Kerosene
20 g Solid Soap
20 g Solid detergent

IV. PROCEDURE

A. Solubility and acidity of carboxylic acids

1. Water solubility
*Perform this test with acetic acid, benzoic acid, and sodium benzoate

a. Place 2 mL water in a test tube.

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

2. Relative acidities of carboxylic acids and phenols

*Perform using benzoic acid and phenol

a. Place 2 mL water in a test tube

b. Add 6 drops of the sample
c. Add 10 drops of 10% NaOH
d. Examine the mixture
e. 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. Place 6 drops or a spatula tip of sample in a test tube

2. Add 3 mL water carefully
3. Observe for any sign of reaction (e.g. heat evolved, bubbles, etc.)
4. 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. 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.

V. CALCULATIONS

a. Preparation of 10% NaOH

= 0.10
1.1
50 ( )
= 5.5

b. Preparation of 10% 3

= 0.10
1.1029
50 ( )
= 5.5145

c. Preparation of 0.05 N HCl

1
( )
36.458
0.05 = 0.05 =
1
250 (1000 )
1
= 0.455725 ( )
1.19
0.38296
=
0.37
= 1.035

d. Preparation of 0.02 M NaCl

58.4428/
0.02 =
50
(1000 )
= 0.0584
 e. Preparation of 0.02 M 2

110.984/
0.02 =
50
(1000 )
= 0.11098

VI. 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.

VII. DESIGNATION AND ASSIGNMENTS

Tasks Members
Preparation of 5 solutions Antonio,Banares,Atos
Preparation of materials Banares
Procedure A &B Antonio,Banares
Procedure C Apuya,Bagacina,Atos
Cleaning Apuya
Distilled water Bagacina
Cleaning Materials Atos