Question

Achiral compound X has the formula C8H17Br. Y, C8H17Cl, is chiral. X undergoes base-promoted E2 elimination to give a single alkene product Z. Under similar conditions Y produces a mixture of alkenes, including Z. Catalytic hydrogenation of Z affords 2-methylheptane. Propose structures for X and Y.

Answer 1

Answer:

1-bromo-6-methylheptane : X

2-chloro-6-methylheptane: Y

Explanation:

A chiral compound is one which has a carbon with all four groups different.

Given:

Compound X is Achiral

Compound Y is chiral

Compound X gives single alkene on elimination : Z

Compound Y gives mixture of alkenes

Z on hydrogenation gives 2-methylheptane.

So the alkene must have carbon chain arrangement similar to 2-methylheptane and so the compound X and Y.

Based on the information the possible compounds are:

1-bromo-6-methylheptane : X

2-chloro-6-methylheptane: Y

The structures are shown in the figure.