Question

Show how you would accomplish the following syntheses using amides as intermediates.

You may use any necessary reagents.

$\text{(c)}\mathbf{cyclopentanecarboxylicacid}\to \mathbf{cyclopentanecarbonitrile}$

Short answer

Syntheses of cyclopentanecarbonitrile from cyclopentanecarboxylic acid and amide as intermediate as given below,

Step-by-step solution

Step-by-Step SolutionStep 1: reaction of carboxylic acid with thionyl chloride (SOCI2)

The carboxylic acid reacts with thionyl chloride $\left({\mathbf{SOCI}}_2\right)$ to give the acetyl chloride as a first product in above reaction.

reaction of acetyl chloride with ammonia (NH3)

In the second step acetyl chloride react with ammonia$\left({\text{NH}}_{\text{3}}\right)$ then there is a formation amide.

Role of POCI3

${\mathbf{POCI}}_3$is a commonly used dehydrating agent in chemical laboratories. It is used as a dehydrating agent in the preparation of nitriles from primary amides.

Synthesis of cyclopentanecarbonitrile from cyclopentanecarbamide i.e. amide as intermediate

When cyclopentanecarbamide react with phosphorus chloride oxide then there is a formation of cyclopentanecarbonitrile.

Synthesis of Cyclopentanecarbonitrile