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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2213

In which of the following does the major organic product contain a stereocentre?

Apropene with $BH X_{3} \cdot THF$ then $H X_{2} O X_{2} / NaOH$
B2-methylbut-2-ene with $Hg (OAc) X_{2}, H X_{2} O$ then $NaBH X_{4}$
Cbut-1-ene with $Hg (OAc) X_{2}, H X_{2} O$ then $NaBH X_{4}$
D2-methylbut-1-ene with $BH X_{3} \cdot THF$ then $H X_{2} O X_{2} / NaOH$

Answer: C, D

But-1-ene gives

CH X_{3} CH (OH) CH X_{2} CH X_{3}

, which has a stereocentre. 2-Methylbut-1-ene gives

HOCH X_{2} CH (CH X_{3}) CH X_{2} CH X_{3}

, which also has one. Propene gives propan-1-ol and 2-methylbut-2-ene gives 2-methylbutan-2-ol, and neither has a stereocentre.

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