Experiment 17

Reaction of Acid Derivatives

Pre laboratory questions
1. Draw the structure of the following compounds: acetyl ahloride,
acetic anhydride, aniline, urea, benzamide, acetyl salicylic acid and
salicylic acid.

aniline Acetyl chloride Acetic anhydride Urea

benzamide Acetyl salicylic acid salicylic acid
Pre laboratory questions
2. What is the purpose of adding ferric chloride to the filtrate of
acetyl salicylic acid?
Ferric chloride is added as an indicator which detects the
presence of salicylic acid in the products. When FeCl3 ionizes, Iron(III)
forms complexes with phenolic compounds, such as salicylic acid. The
color of these complexes range from red to purple.
Pre Laboratory questions
3. How would you test for ammonia vapor in the basic hydrolysis of
amides?
Since it is the vapor that is being tested, the most reliable
method available would be to suspend a damp piece of red litmus
paper at the mouth of the test tube. Ammonia vapor is basic and would
thus turn the red litmus paper blue upon exposure.
Results: Hydrolysis of Acid Chlorides

Acetyl chloride Acetic Anhydride

Water Solution turned warm. No change in temperature

AgNO3 Formed a white precipitate No precipitate formed

Results: Acid Hydrolysis of Acetyl Salicylic Acid
ASA dissolved when the solution was heated
After it was cooled, the solution was then filtered.
FeCl3 was added to the filtrate, and the solution turned purple
Results: Reaction of Amides
Basic Hydrolysis
Acetamide Red litmus paper turned blue
Blue litmus paper did not change
Has pungent odor
Benzamide Red litmus paper turned blue
Blue litmus paper did not change
Acid Hydrolysis
Red litmus paper did not changed
Blue litmus paper turned red
Smells like vinegar
Red litmus paper did not changed
Blue litmus paper turned red
Discussion: Hydrolysis of Acid Chlorides
These derivatives readily react with water to form carboxylic acid.
Hydrolysis for acid chlorides are rapid as compared to the anhydride
which reacts at a slower rate.
Discussion: Hydrolysis of Acid Chlorides
Acetyl Chloride

Addition with AgNO3 produced a cloudy solution.

The precipitate formed is from the reaction between
AgNO3 and HCl, forming AgCl3.
This is done to indicate that a halide ion is present, in this
case Cl
Discussion: Hydrolysis of Acid Chlorides
Acetic anhydride
Discussion: Acid Hydrolysis of ASA

Addition of ferric chloride is done in order to detect the presence of a

phenolic group.
The purple coloration results from the formation of ferric salicylate
complexes.
Discussion: Reaction of Amides
Basic Hydrolysis

Acetamide

Acid Hydrolysis
Questions
1. Write the equations that describes the reaction mechanism for the
hydrolysis:
a. Acetyl Chloride
Questions
b. acetic anhydride
Questions
2. Explain why acetyl chloride reacts faster with water than acetic
anhydride.
Acetyl chloride has a good leaving group which is the chlorine
because of this the electrophilicity of the carbonyl C is greater than the
electrophilicty of the carbonyl C in acetic anhydride
Questions
3. Write the equation for the hydrolysis of acetylsalicylic acid
Questions
4. Account for the different odors and reaction toward litmus of the
volatile product obtained when acetamide is hydrolyzed in acid and
in base.
Acid hydrolysis

Smells like vinegar because of acetic acid

Blue litmus paper turned red because of presence of acid
Questions
Basic hydrolysis

Presence of NH3 produces a pungent odor

Red litmus paper turns blue because of ammonia vapor