JEE Advanced 2023 Paper 1 · Q16 · Isomerism & Stereochemistry
Match the reactions in List-I with the features of their products in List-II. (P) primary alkyl bromide + aq NaOH at a chiral neopentyl-type C; (Q) secondary alkyl bromide $CH_3$-$CH(Br)$-$CH_2$-$CH_2$-$CH_3$ + aq NaOH (S$_N$2); (R) tertiary alkyl bromide + aq NaOH (S$_N$1) at a stereocenter; (S) allylic bromide + aq NaOH giving an S$_N1'$/S$_N1$ pair. List-II: (1) Inversion of configuration, (2) Retention of configuration, (3) Mixture of enantiomers, (4) Mixture of structural isomers, (5) Mixture of diastereomers
Reveal answer + step-by-step solution
Correct answer:B
Solution
(P) S$_N$2 at a neighbouring chirality-preserving site: retention — (2). (Q) S$_N$2 at a stereocenter inverts configuration — (1). (R) S$_N$1 at a stereocenter goes via planar carbocation, gives racemic mixture (mixture of enantiomers) — (3). (S) Allylic rearrangement (S$_N$1 + S$_N1'$) gives diastereomeric products if a second stereocenter is present — (5).
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