Which one of the following compounds does not react with acetyl chloride?

Which one of the following compounds does not react with acetyl chloride?
  1. $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{NH}_2$
  2. $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{NHCH}_3$
  3. $\left(\mathrm{CH}_3 \mathrm{CH}_2\right)_3 \mathrm{~N}$
  4. $\left(\mathrm{CH}_3\right)_3 \mathrm{CNH}_2$

Solution

Aliphatic and aromatic primary and secondary amines undergo acylation reaction as these amines contain replaceable hydrogen atoms (positively polarised H ) on the nitrogen atom. Triethylamine, i.e., $\left(\mathrm{CH}_3 \mathrm{CH}_2\right)_3 \mathrm{~N}$ is a tertiary amine, without any replaceable H -atom. Thus, it will not react with acetyl chloride.

Asked in: MHT CET 2024 (09 May Shift 2)

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