An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.
An organic acid P(C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.
The compound S is
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
The alternative reaction sequence from P produces compound S.
From the reaction scheme shown in the passage, P undergoes:
Reduction (likely of the carboxylic acid to an amine via intermediate steps)
The product is an amine derivative
Based on the structures provided and the reaction conditions, compound S is N-methyl-4-isobutylaniline (the amine is on the benzene ring at the para position to the isobutyl group, with a methyl substituent on the nitrogen).
Correct answer: (B)
JEE Advanced · 2018 · 20 May 2018 · Paper 1 · Single correct option
