JEE Main · 2016 · 03 Apr 2016 · Offline · Haloalkanes and Haloarenes

2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields :

(A)(see structures)
b
c
(B)(see structures)
(C)(see structures)
(D)All of these✓ Correct

Answer: (D)

Solution

2-chloro-2-methylpentane is a tertiary halide, and sodium methoxide is both a strong base and a nucleophile, so it can substitute to give an ether and eliminate to give alkenes. Elimination can take a hydrogen from either neighbouring carbon, giving the more substituted 2-methyl-2-pentene as the major Saytzeff product and 2-methyl-1-pentene as the minor one. Since the substitution ether and both alkenes all form, every one of the listed products results.

JEE Main · 2016 · 03 Apr 2016 · Offline · Single correct option

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