Question

Two products, A and B, are obtained from the reaction of 1-bromobutane with NH₃ . Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.

Short answer

Reaction followed as:

Formation of Compound A

Formation of Compound C

Formation of Compound D

Step-by-step solution

Formation of compounds A and B

As given the reaction of 1-bromobutane with ammonia leads to produce A and B compound.

The bromobutane on reacting with ammonia leads to produce primary amine that is butylaminethat’s compound A and which further on reacting with bromobutane leads to produce secondary amine dibutyl amine that’s compound B as shown below:

Formation of Compound B

Formation of compound C

As given compound Cis produced on the reaction of acetyl chloride with compound A which is butylamine. So, the reaction of butylamine on reacting with acetyl chloride produces amide as shown:

Formation of Compound C

And also confirmed by IR spectra shows absorption ~3300shows N-H stretching.

Formation of compound D

Compound D is produced on the reaction of acetyl chloride with compound B which is a di-butyl amine. So, the reaction of butylamine on reacting with acetyl chloride produces amide as shown:

Formation of Compound D

And also confirmed by IR spectra do not show absorption ~3300that is the absence of N-H stretching that it is a secondary amine.