The ketone shown is reduced with sodium borohydride to an alcohol. Using configurational isomers of the alcohol's constitution as the counting convention, how many stereoisomers does the alcohol have?

Answer: A

3-Methylpentan-2-one is reduced to 3-methylpentan-2-ol. This alcohol has two stereocentres (C-2 and C-3), which are not related by symmetry, so it has

2^{2} = 4

stereoisomers (two pairs of enantiomers). RDKit enumeration of the product gives 4.

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