Experiment 8 Pre-Lab Comparative Reactions of Carboxylic Acid Derivatives

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EXPERIMENT 8 Pre-lab

COMPARATIVE REACTIONS OF CARBOXYLIC ACID DERIVATIVES

Group number Section Score


Seat number Name Date

1. Arrange the following acyl compounds in decreasing order of reactivity towards a nucleophile.
(1 being the most reactive)
______ carboxylic acid amide
______ carboxylic acid halide
______ carboxylic acid ester
______ carboxylic acid
______ carboxylic acid anhydride

2. Rationalize the order of reactivity based on the answers in #1.

3. Write the general formula that describes each carboxylic acid derivative in #1.

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EXPERIMENT 8 Data sheet
COMPARATIVE REACTIONS OF CARBOXYLIC ACID DERIVATIVES

Group number Section Score


Seat number Name Date

A. Hydrolysis
Observations
Sample
Warming effect Reaction with 2% AgNO3 Reaction with sat’d. NaHCO3
Acetyl chloride

Acetic anhydride

Ethyl acetate Odor:

Benzamide Color change in litmus paper:

B. Alcoholysis: Ester Formation


Sample Odor Formation of layers

Acetyl chloride

Acetic anhydride

C. Aminolysis: Anilide Formation


Sample Color of precipitate formed

Acetyl chloride

Acetic anhydride

D. Hydroxamic Acid Test for Carboxylic Acid Derivatives


Sample Color of resulting mixture

Acetyl chloride

Acetic anhydride

Ethyl acetate

Benzamide

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EXPERIMENT 8 Post-lab
COMPARATIVE REACTIONS OF CARBOXYLIC ACID DERIVATIVES

Group number Section Score


Seat number Name Date

1. Formulate a general reaction for each of the carboxylic acid derivatives with the corresponding
nucleophile for the following reactions: hydrolysis, alcoholysis, aminolysis and the hydroxamic acid
test.

2. Which among the carboxylic acid derivatives studied in the experiment provided the best leaving
group? Why?

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