(CH_3)_3C–CH=CH_2 (3,3-dimethylbut-1-ene) [ (ii) NaBH _4/ NaOH ] (i) Hg(OAc) _2/ THF A. A is

JEE Main Chemistry question

(CH)C–CH=CH (3,3-dimethylbut-1-ene) . is

(A)2,3-Dimethylbutan-2-ol (the rearranged product)
(B)3,3-Dimethylbutan-2-ol (unrearranged)Correct
(C)2,2-Dimethylbutan-1-ol
(D)3,3-Dimethylbutane-1,2-diol

Answer: (B)

Solution

Oxymercuration proceeds through a bridged mercurinium ion rather than a free carbocation, so no 1,2-alkyl shift can occur. Markovnikov addition of "OH" to the internal carbon, followed by demercuration, gives the simple,

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Question ID VK-142627