Q20P - Organic Chemistry (Mcmurry)

Question

How would you convert N-ethylbenzamide to each of the following products?

 (a) Benzoic acid (b) Benzyl alcohol (c) ${\mathbf{C}}_{\mathbf{6}}{\mathbf{H}}_{\mathbf{5}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{NHCH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{3}}$

Step-by-Step Solution

Answer

Reactants needed are:

1. methyl benzoate and Methyl magnesium bromide 
2. methyl acetate and aryl magnesium bromide 
3. methyl pentanoate and ethyl magnesium bromide

Step 1: Hydrolysis of Amide

On hydrolysis amides produces carboxylic acids. So, the reaction can be given as

 

Step 2: Hydrolysis followed by reduction

For preparing alcohol from amide first convert the amide to acid by hydrolysis and then acid can be reduced to alcohol using LiAlH₄.

Step 3: Reduction of Amide

Amides on reduction with LiAlH₄ convert to amines. So, the reaction can be given as