JEE Main levelSingle correct optionDifficulty 2 of 3o3140
Match the neighbouring group in List I with the cyclic intermediate in List II. List I: P the carboxylate group of 2-bromopropanoate; Q the sulfide sulfur of CHX3S−CHX2CHX2−Cl; R the tertiary nitrogen of (CHX3)X2N−CHX2CHX2−Cl; S the benzene ring of CX6HX5−CHX2CHX2−OTs. List II: 1 aziridinium ion; 2 phenonium ion; 3 alpha-lactone; 4 episulfonium ion.
AP-3, Q-1, R-4, S-2
BP-4, Q-3, R-1, S-2
CP-2, Q-4, R-1, S-3
DP-3, Q-4, R-1, S-2
Answer: D
Carboxylate oxygen gives a three-membered alpha-lactone; sulfur gives an episulfonium ion; nitrogen gives an aziridinium ion; the pi system of a phenyl ring gives a bridged phenonium ion (a spiro cyclohexadienyl cation).