JEE Main 2021 · 27 August · evening · Single correct · +4 / −1
The correct structures of A and B formed in the following reactions are :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (d)
Solution
Chemistry ma’am · 4 steps
Reduce the nitro group first, then let the more nucleophilic NH₂ grab the one acetyl group.
- Find A. H₂/Pd in ethanol reduces only the -NO₂ group to -NH₂. The -OH is untouched, so A is p-aminophenol, HO-C₆H₄-NH₂.
- Compare nucleophiles. A now has two groups that can attack acetic anhydride, -NH₂ and -OH. Nitrogen is less electronegative than oxygen, so its lone pair is more available and -NH₂ is the stronger nucleophile.
- Only one equivalent. With just 1.0 eq of (CH₃CO)₂O, there is only enough reagent for one acylation, and the faster -NH₂ uses it up. The product is the amide HO-C₆H₄-NHCOCH₃, which is paracetamol.
- So. A is p-aminophenol and B is N-(4-hydroxyphenyl)acetamide, with the -OH still free. That is option (d).
The idea to keep. When a molecule has both -NH₂ and -OH and you add one equivalent of an acylating agent, the amine reacts first. You get the amide, not the ester.
Answer from the NTA final answer key. Solution by PrepWiser.