EXPERIMENT NO.

12
ACYL COMPUNDS: SOAPS AND DETERGENTS
I.

INTRODUCTION

II.

RESULTS AND DISCUSSION

A. Solubility and Acidity of Carboxylic Acids
1. Water Solubility (+ miscible)
Sample

Observation

Reaction with blue litmus

paper
Blue; Basic
Red; Acidic

Acetic acid
(+) clear, colorless
Benzoic acid
(-) clear, colorless
Sodium
(+) clear, colorless
Blue; Basic
Benzoate
Carboxylic acids are substances that have a general formula of RCO 2H. They are
considered as Bronsted-Lowry acids or proton donors. They are polar since they can be
both be hydrogen-bond acceptor and donors due to the presence of the carbonyl and
hydroxyl groups respectively. There are instances that the hydroxyl and carbonyl group
have the tendency to self-associate and become less soluble if the carbon no increases.
In the experiment, all the samples are soluble in water except for benzoic acid.
Acetic acid, CH3COOH, and sodium benzoate, NaHCO 3, are very polar thus they are soluble
in water. Benzoic acid did not dissolve because it contains greater number of carbon
atoms (C6H5COOH). Sodium Benzoate is the least soluble among them since it is slightly
alkaline due to the formation of carbonic acid and hydroxide ion.
2. Relative Acidities of Carboxylic Acids and Phenols
Sample

Reaction with 10%

NaOH

Benzoic Acid

heterogeneous

Phenol

2 layers are visible

Jelly like liquid forms at
the bottom

Reaction with 10 %
NaHCO3
appearance
of
bubbles
Jelly like liquid forms
at the bottom

B. Hydrolysis of Acyl Compounds

Sample

Sign of reaction

Test with Blue Litmus

Paper

Heat
evolved;
Acetyl Chloride
bubbles
formed Red; Acidic
(unheated)
No
reaction
Acetic Anyhydride
Red; Acidic
(heated)
No
reaction
Benzamide
Blue; Basic
(heated)
Hydrolysis is the reaction of organic compound with water wherein a bond in an
organic molecule is broken as well with the O-H bond of water molecule. Since acyl group
is derived from carboxylic acid, they will become carboxylic acids when they undergo
hydrolysis. Acetyl chloride (CH3COCl) is an acyl chloride that reacts vigorously with water
becoming rapidly hydrolyzed. Steamy white fumes of hydrogen chloride can be seen. That
is why in the experiment, heat evolved from the test tube. Acetic anyhydride ((CH 3CO)2O)
is the simplest isolatable of acid anhydride. When it dissolves in water, it has a limited
stability because it hydrolyses to give acetic acid. Theres no sign of reaction in the
experiment but there was a reaction which probably cannot be obviously seen. Benzamide

(C6H5CONH2) is a derivative of benzoic which is less soluble in water than the previous
samples due to higher number of carbon atoms compared to acetic chloride and acetic
anhydride. Since it contains an amide, it is basic.
C. Saponification of Coconut Oil
Saponification is the base-promoted hydrolysis of fats and oils producing glycerol
and a mixture of fatty acid salts called soaps. In the preparation of soaps, coconut oil
which has triglycerides are heated near to boiling with NaOH. At molecular level,
saponification corresponds to the base - promoted hydrolysis of the ester groups in
trigylcerides. After the hydrolysis is complete, sodium chloride is added to precipitate
sodium salts as thick curds of soap.
D. Comparison of Soaps and Detergents
1. Hydrolysis
Sample

Test with red litmus

Test with blue litmus
paper
paper
Detergent
Red to blue
Blue to blue
Soap
Red to blue
Blue to blue
Soap is dissolved in warm water because of its insolubility in water and gives a
colloidal mixture while synthetic detergents are mostly LAS or liner alkyl-benzenesulfonates; both are basic when tested on litmus paper.
2. Reaction with Acid
Sample
Observation
Detergent
Bubbles rising, colorless layer (clear)
Soap
Cloudy mixture; white precipitate
Soaps are also less effective in acidic water compared to detergents (synthetic
detergents soluble in both acidic and alkaline solutions). The long hydrocarbon chains of
natural soaps are insoluble in water, they tend to cluster in such a way to minimize
contact with water and thus form water-insoluble salts especially when ions such as
calcium, magnesium, and iron are present in water.
3. Reaction with Soft and Hard Water
Sample
Detergent

NaCl
Clear solution

CaCl2
Cloudy solution
Clear solution; white
Soap
Cloudy solution
precipitate
Due to the presence of Ca(II) ions in water, for soap, there is less tendency for soaps
to produce bubbles and the nonpolar hydrocarbon inner parts of soap micelles has less
tendency to dissolve nonpolar dirt molecules. Detergents are not greatly affected by hard
water or presence of Ca(II)ions and other mineral ions present in water since they are
synthetically made with 12-20 carbon atoms long and a polar group at one end of the
molecule that does not form insoluble salts.
4. Emulsifying Action
Sample
Detergent
Soap
Water Blank

Observation
Emulsified; less cloudy; more
froth
Turbid layer; less emulsions; less
froth
Two separate layers; did not
emulsify

In the experiment, detergent has emulsification, while soap, has turbid layer while
the water has nothing at all. This means that detergents are not greatly affected by hard
water or presence of Ca(II)ions and other mineral ions and can still convert the soluble
sodium carboxylates are converted into insoluble metal salts. While soap has turbid layer
which means it emulsified less, and water as least among them all to emulsify.
III.
IV.

CONCLUSION
REFERENCES/BIBLIOGRAPHY
Chem 33.1 Laboratory Manual
Chem 33.1 Course Syllabus
Kowens. (2006). Solubility of Organic Compounds. North Seattle: FacWeb

V.

ANSWERS TO 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 CHCl 3? Explain.
The difference in the solubility of benzoic acid and sodium benzoate in water is
their polarity. Benzoic acid is non-polar while sodium benzoate is polar. With this, only
sodium benzoate is soluble in polar water. Their difference is due to their molecular
structure. Benzoic acid is an aromatic carboxylic acid while sodium benzoate is a
combination of alkali metal with carboxylic acids. CHCl 3 is polar so sodium benzoate is
predicted to be soluble on it.
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.
In order of increasing acidity: water < alcohol < phenol < carboxylic acid
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.
The order of decreasing hydrolysis rate is: acid halides > acid anhydrides >
esters > amides. This is based on their acidities where acid-halide as the more acidic
so it can hydrolyze more, and due to the presence of amine in amides, its the most
basic and cant readily hydrolyze.
4. Is the soap water mixture a true solution? Cite examples to support your answer.
The soap water mixture is considered to be colloidal thats why it is not a
solution. The soap solute present in water is not homogenous or totally dissolved in
water. This can be seen if light is passes directly to the mixture, and the scattering of
light would then be observed. The composition and physical properties vary from one
part of the mixture to another. If the soap water mixture is subjected to a beam of light,
a Tyndall effect will take place. The evident scattering of light is not a characteristic of a
true solution, but rather a quality of colloidal dispersion.
5. What is a colloidal mixture? How does a colloidal mixture arise when soap is mixed
with water?
A colloidal mixture is a mixture wherein particles which the mixture contains is
larger than normal solute but smaller enough to remain suspended in the dispersing
medium. Colloidal mixture arises when soap is mixed with water because the particles
tend to attach more with each other than in well dispersed in 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.

In the experiment, both soap-water and detergent-water mixtures are basic.

7. Which would you predict to have a greater emulsifying power in hard water, soaps or
synthetic detergent? Explain.
Having greater emulsifying power means, it has greater cleaning power; this
means more insoluble dirt can be removed. However, hard water can affect the ability
of soap to emulsify with the presence of hard minerals such as Mg 2+, and Ca2+.
However, detergent has greater emulsifying power since it is not greatly affected by
minerals by hard water because it can still convert the soluble sodium carboxylates are
converted into insoluble metal salts.
8. Explain the cleaning property of soaps and detergents based on your observations of
their emulsifying action.
Based on the emulsifying property of soaps and detergents, detergents can be
more effective compared to soaps since hard water is unavoidable. Due to the
presence of Ca(II)ions in water, for soap, there is less tendency for soaps to produce
bubbles and the nonpolar hydrocarbon inner parts of soap micelles has less tendency
to dissolve nonpolar dirt molecules. On the other hand, Detergents are not greatly
affected by hard water or presence of Ca(II)ions and other mineral ions present in water
since they are synthetically made with 12-20 carbon atoms long and a polar group at
one end of the molecule that does not form insoluble salts.