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Question
Illustrate the following reactions giving suitable example in each case
Acetylation of amines
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Solution
Acetylation of amines: Acetylation is the process of introducing an acetyl group into a molecule. Aliphatic and aromatic primary and secondary amines undergo the acetylation reaction by nucleophilic substitution when treated with acid chlorides, anhydrides or esters. This reaction involves the replacement of the hydrogen atom of the −NH2 or > NH group by the acetyl group, which, in turn, leads to the production of amides. To shift the equilibrium to the right-hand side, the HCl formed during the reaction is removed as soon as it is formed. This reaction is carried out in the presence of a base (such as pyridine), which is stronger than the amine.
For example, the reaction of benzenamine with acetyl chloride in the presence of pyridine yields N-phenylethanamide.
\[{C_6 H_5 - {NH}_2}_{Benzenamine} + {{CH}_3 - CO - Cl}_{Acetyl chloride} \to^{Pyridine} {C_6 H_5 - NH - CO - {CH}_3}_{{N - Phenylethanamide}_\left( Soluble in alkali \right)} + HCl\]
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RELATED QUESTIONS
Give reasons for the following:
Aniline does not undergo Friedel- Crafts reaction.
Write the chemical equations involved when aniline is treated with the following reagents:
Br2 water
Account for the following:
Although the amino group is o, p-directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
How will you convert the following?
Aniline into N−phenylethanamide
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Reason (R): Carboxyl group increases the electron density at the meta position.
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Identify the major product C formed in the following reaction sequence:
\[\ce{CH3 - CH2 - CH2 - I ->[NaCN] A ->[OH-][Partial hydrolysis] B ->[NaOH][Br2] \underset{(major)}{C}}\]
