There are five constitutional isomers with the molecular formula C6H14. When treated with chlorine at 300°C, isomer A gives a mixture of two monochlorination products. Under the same conditions, isomer B gives a mixture of five monochlorination products, isomer C gives four monochlorination products, and isomer D gives a mixture of three monochlorination products. From this information, draw the structural formula of isomer D.

Pentane or 2,2-dimethylbutane  

Explanation:

I've numbered the isomeric hexanes from 1 to 5 and labelled the sets of equivalent hydrogens.

The results are

Isomer 1— three sets of equivalent hydrogens

Isomer 2— five sets of equivalent hydrogens

Isomer 3— four sets of equivalent hydrogens

Isomer 4— two sets of equivalent hydrogens

Isomer 5— three sets of equivalent hydrogens

Each set will give one monochloro substitution product.

4 = A. Two monochloro isomers.

2 = B. Five monochloro isomers.

3 = C. Four monochloro isomers.

Isomers 1 and 5 each give three monochloro isomers.

Thus, we cannot assign Structure D definitively.

D is either pentane or 2,2-dimethylbutane.

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