Group Members: Curso, Mark Anthony R.

Lambojon, Cyril Marie J.

Oro, Clyde Princess Khim V.

Date of Experiment: April 25, 2015

Experiment No. 9
Acyl Compounds: Soap and Detergents

I.

Results and Discussions.

Solubility and Acidity of Carboxylic Acid
Sample

Solubility Behavior

Blue Litmus Paper to:

Acetic Acid

soluble

red

Benzoic Acid

insoluble

red

Sodium Benzoate

soluble

blue

Acetic acid and sodium benzoate were both soluble in water while the benzoic acid was
not. Carboxylic acids form new carbonyl compound when water is added to it by nucleuphilic
acyl substitution. C=O bond in benzoic acid is electron-rich which made it unready to react with
the nucleophile, water. In acetic acid and sodium benzoate, their C=O bond is electron-poor
making it ready to react with the nucleuphile, water.

Relative Acidities of Carboxylic Acids and Phenols

Sample

Solubility in
10% NaOH

10% NaHCO3

Benzoic Acid

Soluble

Soluble

Phenol

Soluble

Insoluble

Carboxylic acids are soluble in dilute solutions of both strong acid and strong base.
Benzoic acid is a carboxylic organic acid compound, thus, it is soluble in 10% NaOH and 10%
NaHCO3. On the othetr hand, phenols are soluble in dilute solutions of strong base but insoluble
in dilute solution of 10% NaHCO3.

Hydrolysis of Acyl Compounds

Sample

Reaction with H2O

After heating

Blue Litmus Paper to:

Acetyl Chloride

Cloudy, bubbles formed

No change

red

Acetic Anhydride

Clear, homogeneous

No change

red

Benzamide

insoluble

Dissolved, clear solution

red

Acetyl chloride reacts with water to yield carboxylic acid by substituting the -Cl with
-OH. Acid anhydride reacts with water forming two acids. Reaction of benzamide and water
requires heat to yield acid and amine. Acetyl chloride, acetic anhydride and benzamide are
acidic. Ethyl benzoate is basic.
Comparison of Soap and Detergent
Sample

Hydrolysis

Reaction
with HCl

Reaction with
Soft H2O

Hard H2O

Red Litmus
Paper to:

Blue litmus
Paper to

Soap

blue

blue

Cloudy
liquid

Clear liquid
with bubbles

Cloudy liquid with

suspended particles and
smaller bubbles

Detergent

blue

blue

Clear liquid

Clear liquid
with bubbles

Clear liquid with bubbles

Soap and detergents are alkaline solutions thus it will give a blue color to a litmus paper.
Soap solutions are found to have a turbid solution while detergents have a clear solution in HCl.
Soap in soft water resulted to a clear liquid since it is an effective cleanser on soft water. Soap
in hard water has a cloudy liquid since it is an ineffective cleanser in hard water. On the other
hand, detergent is an effective cleanser in both soft and hard water, as a result, clear liquid is
observed in detergent in both soft and hard water.
Emulsifying Reaction
Sample

Observations

Soap

Two distinct layers, white particles on upper part,white liquid in

lower part and smaller bubbles formes

Detergent

Two distinct layers, white liquid on the upper part slightly cloudy
liquid on lower part and bubblew formed

Water

No emulsification

Detergent has more emulsification than soap while water has none.

II. Calculations. There are no calculations in this experiment.

III. Questions and Answers.
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
Carboxylic acids form new carbonyl compound when water is added to it by
nucleuphilic acyl substitution. C=O bond in benzoic acid is electron-rich which made it unready
to react with the nucleophile, water. Thus, benzoic acid is insoluble in water. In acetic acid and
sodium benzoate, their C=O bond is electron-poor making it ready to react with the nucleuphile,
water. Thus, acetic acid and sodium benzoate are soluble in water.
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.
Carboxylic acids are much more acidic than alcohols even though both contain OH
group due to the relative stabilities of carboxylate anions and alkoxide anions. In carboxylate
ion, the negative charge is delocalized, or spread out over both oxygen atoms while in alkoxide
ion, the negative charge is localized on one oxygen atom only. Thus, a carboxylate ion is a
stabilized resonance hybrid of two equivalent structures.
Phenols are more acidic than alcohols because the phenoxide anion is resonancestabilized by the aromatic ring. Sharing the negative charge over the ring increases the stability
of the phenoxide anion and thus increases the tendency of the corresponding phenol to
dissociate. However, water is more acidic than alcohol because water can delocalize its negative
charge. Therefore, carboxylic acids > phenols > water > alcohols in terms of their acidities.
3. Based on the results in Part B, arrange the following compound types in order of decreasing
hydrolysis rate: acid halides, acid anhydrides, esters and amides. Give theoretical explanations
for the observed differences in reaction rates.
Based on the results in part B, acid halides have the highest hydrolysis rate because acid
halides are polar, and the more highly polar compound are the more reactive it is. Acid halides
is also the most reactive because it strongly polarizes the carbonyl group due to its
electronegativity. Acid anhydrides are next in order because it reacts just like the acid halides,
but in a slower rate. During the nucleophilic acyl substitution step, only half of the molecule is
used and the other half acts as the leaving and produces a by-product called carboxylate anion.
Esters are next in order because it also reacts in the same manner with the first two compounds,
although esters are less reactive toward nucleophiles than acid chlorides or anhydrides. The last
in order are the amides because they have a very stable linkage enough to serve as the basic unit
from which proteins are made.

4. Is the soap water mixture a true solution? Cite examples to support your answer.

The soap water mixture is not a true solution but a colloidal mixture. The soap water
mixture is a cloudy mixture where one substance is evenly dispersed throughout one another.
With this, some colloids are mistaken to be true solutions due to their similar appearances.
5. What is a colloidal mixture? How does a colloidal mixture arise when soap is mixed with
water?
A colloidal mixture is a mixture that has two subsatnces equally or evenly dispersed
with each other. A colloidal mixture has an outer layer with the same charges causing them to
repel each other resulting to lesser aggregation to form particles that are large enough to
precipitate.
The non-polar hydrocarbon tail of the soap dissolves into the oil, a non-polar
hydrocarbon, forming spherical cluster called micelles. Micelles' negatively charged surfaces
are where droplets of oil are solubilized in water where they become coated by the hydrophobic
non-polar tails of soap molecules. As a result, a colloidal misture of soap-water mixture arise.
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 of the reactions of the soap-water and detergent-water
mixtures to litmus paper.
Reaction of both soap-water and detergent-water mixtures to litmus paper shows their
alkalinity. Soaps tend to be alkaline after they undergo hydrolysis reaction upon hydration.
Detergent-water mistures are also alkaline in a lesser degree.
7. Which would you predict to have a greater emulsifying power in hard water, soaps or
synthetic detergent. Explain.
Synthetic detergents have a greater emulsifying power in hard water'' because it does
not form precipitates when introduced with the calcium and magnesium ions. This is due to the
presence of sulfonate group in detergents, which cannot be found in soaps.
8. Explain the cleaning property of soaps and detergents based on your observations of their
emulsifying action.
The soaps' and detergents' ability to emulsify or disperse water-insoluble compounds
and hold them in suspension with water is a result of their cleaning action. When a soap or
detergent is added to water that contains water-insoluble compounds, the soap or detergent
molecules sorround the water-insoluble compounds. The water-insoluble compounds are then
dissolved in the alkyl groups of the soap or detergent molecules while their ionic end allows the
micelle to dissolve in water.
IV. Conclusion
The group compared the acidities of carboxylic acids and phenols and found out that
carboxylic acids are more acidic than phenols, this is due to the relative stabilities of
carboxylate anions and alkoxide anions. The group also prepared soap and learned that
preparation of such is by saponification of fats. The group also campared the properties of soap
and detergents and found out that detergents compared to soap are more effective in hard
water.