3,3-Dimethylbut-1-ene is treated with Hg(OAc)2 in THF/H2O, followed by NaBH4. The major product is

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JEE Main levelSingle correct optionDifficulty 2 of 3ap006

3,3-Dimethylbut-1-ene is treated with $Hg (OAc) X_{2}$ in $THF / H X_{2} O$ , followed by $NaBH X_{4}$ . The major product is

A3,3-dimethylbutan-2-ol
B2,3-dimethylbutan-2-ol
C3,3-dimethylbutan-1-ol
D2,3-dimethylbutan-1-ol

Answer: A

Oxymercuration-demercuration gives Markovnikov hydration through a mercurinium ion, so no carbocation rearrangement occurs. OH goes to the more substituted alkene carbon (C-2), giving 3,3-dimethylbutan-2-ol.

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3,3-Dimethylbut-1-ene is treated with Hg(OAc)X2​ in THF/HX2​O, followed by NaBHX4​. The major product is

Answer: A

More questions on Preparation of alcohols including from carbonyls and Grignard

3,3-Dimethylbut-1-ene is treated with $Hg (OAc) X_{2}$ in $THF / H X_{2} O$ , followed by $NaBH X_{4}$ . The major product is