Counting enantiomers as separate compounds, how many monochlorination products (all stereoisomers included) can the alkane shown give?

Answer: B

2,2-Dimethylbutane has three sets of equivalent hydrogens (the three methyls on C-2, the CH2, and the ethyl CH3), so there are three constitutional monochlorides: 1-chloro-2,2-dimethylbutane, 2-chloro-3,3-dimethylbutane and 1-chloro-3,3-dimethylbutane. Only 2-chloro-3,3-dimethylbutane, with chlorine on the former CH2 carbon, has a stereocentre and exists as two enantiomers. Total: 1 + 2 + 1 = 4 (RDKit enumeration gives 4).

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