Question

Problem:What acyl chloride and amine are required to synthesize the following amides?

a. N-ethylbutanamide b. N,N-dimethylbenzamide

Short answer

Answer

a.

b.

Step-by-step solution

Acid chloride to amide

Amide is synthesized from the acid derivate, and themost reactive acid derivate is acid chloride.

The acid chloride reaction with the neutral amine (with at least one N-H group) is nucleophilic,attacking the carbonyl carbon of acid chloride to form atetrahedral intermediate,leaving chlorineformation of the desired amide.

Formation of N-ethylbutanamide

(acid chloride) reacts with the two moles of (amine) reaction goes by a nucleophilic addition-elimination mechanism.The nucleophile amine will attack the carbonyl carbon, leaving group (chloride). Finally, deprotonation forms the desired product, N-ethylbutanamide.

The reaction between the and the is shown below

 Step 3: Formation of N,N-dimethylbenzamide

Acid chloride reacts with the two moles of (amine)reaction goes bya nucleophilic addition-elimination mechanism. The nucleophile amine will attack the carbonyl carbon, leaving group (chloride) leave, and finally, deprotonation forms the desired product, N,N-dimethylbenzamide.

The reaction between the and the is shown as follows.

Formation of N,N-dimethylbenzamide