Question

Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C7H14 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15I products; in this reaction Y reacts faster than X. What is the structure of X?

Answer 1

Answer:

X  is 3-chloro-2,4-dimethylpentane

Explanation:

The radical chlorination of 2,4-dimethylpentane may give three products.

Based on the information that

i) both the products gives single alkene on elimination and

ii) both the products also undergoes SN2 reaction but Y reacts faster than X

We may conclude that as SN2 reaction is faster in primary alkyl halides as compared to secondary or tertiary so Y must be primary or secondary and it cannot be tertiary alkyl halide.

The possible products are shown in the figure.

The structure of X is shown in the figure.