For which alkene do Hg(OAc)2/H2O then NaBH4 and dilute H2SO4 give the same alcohol, while BH3.THF then H2O2/NaOH gives a different alcohol?

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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2203

For which alkene do $Hg (OAc) X_{2} / H X_{2} O$ then $NaBH X_{4}$ and dilute $H X_{2} SO X_{4}$ give the same alcohol, while $BH X_{3} \cdot THF$ then $H X_{2} O X_{2} / NaOH$ gives a different alcohol?

Acyclohexene
B3,3-dimethylbut-1-ene
C1-methylcyclohexene
D3-methylbut-1-ene

Answer: C

1-Methylcyclohexene gives 1-methylcyclohexan-1-ol by both Markovnikov methods and 2-methylcyclohexan-1-ol by hydroboration. For cyclohexene all three give cyclohexanol. The two branched terminal alkenes give a rearranged alcohol with acid but not with oxymercuration.

Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on Carbocation rearrangements in addition

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For which alkene do Hg(OAc)X2​/HX2​O then NaBHX4​ and dilute HX2​SOX4​ give the same alcohol, while BHX3​⋅THF then HX2​OX2​/NaOH gives a different alcohol?

Answer: C

More questions on Carbocation rearrangements in addition

For which alkene do $Hg (OAc) X_{2} / H X_{2} O$ then $NaBH X_{4}$ and dilute $H X_{2} SO X_{4}$ give the same alcohol, while $BH X_{3} \cdot THF$ then $H X_{2} O X_{2} / NaOH$ gives a different alcohol?