Q2 / 180 · COMEDK 2024 (Morning Shift) · Chemistry
What is the final product formed when Toluene undergoes the following series of reactions?
- A3-methylaniline
- B3-methylacetanilde
- Correct answerC4-methylacetanilide
- D3-Chloro-acetanilide
Solution
Toluene reacts with conc. $HNO_{3}$ and $H_{2}SO_{4}$ (nitrating mixture) to undergo electrophilic aromatic substitution. Since the methyl group is ortho/para directing, the major product [B] is p-nitrotoluene.
Reduction of p-nitrotoluene with $Fe/HCl$ converts the nitro group ($-NO_{2}$) into an amino group ($-NH_{2}$), yielding [C], which is p-toluidine (4-methylaniline).
Reaction of p-toluidine with acetic anhydride $(CH_{3}CO)_{2}O$ results in the acetylation of the amino group to form [D], which is 4-methylacetanilide.
Answer: 4-methylacetanilide
Reduction of p-nitrotoluene with $Fe/HCl$ converts the nitro group ($-NO_{2}$) into an amino group ($-NH_{2}$), yielding [C], which is p-toluidine (4-methylaniline).
Reaction of p-toluidine with acetic anhydride $(CH_{3}CO)_{2}O$ results in the acetylation of the amino group to form [D], which is 4-methylacetanilide.
Answer: 4-methylacetanilide
Hence, the correct answer is option: 'C'.