The compound shown is completely hydrogenated (H2, Ni) to an alkane. How many different monochlorination products can that alkane give? Count constitutional isomers only and ignore stereoisomers.

The compound is 2,4-dimethylpent-2-ene; hydrogenation gives 2,4-dimethylpentane. This alkane has three hydrogen sets: the four equivalent methyls, the two equivalent CH groups and the CH2. So 3 monochloro products.