The ketone shown is converted into an alcohol. Select the reagent(s), each followed by aqueous work-up where needed, that convert it into a secondary alcohol.

A $NaBH X_{4}$
B $LiAlH X_{4}$
C $CH X_{3} MgBr$
D $NaCN / H X^{+}$

Answer: A, B

Butanone gives butan-2-ol, a secondary alcohol, on hydride reduction with either sodium borohydride or lithium aluminium hydride. Methylmagnesium bromide and HCN add a carbon nucleophile to the carbonyl carbon, giving tertiary alcohols (the cyanohydrin has a tertiary OH).

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