Reaction of t-butyl bromide with sodium methoxide produces

JEE Main Chemistry question

Reaction of -butyl bromide with sodium methoxide produces

(A)Isobutane
(B)IsobutyleneCorrect
(C)Sodium -butoxide
(D)-butylmethyl ether

Answer: (B)

Solution

Sodium methoxide, , is a small but strong and significantly basic nucleophile. With a tertiary substrate like -butyl bromide, severe steric hindrance at the crowded tertiary carbon disfavours backside attack, so the strongly basic methoxide instead removes a -hydrogen in an E2 elimination,

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Question ID VK-148031