Question

Compound W, C6H11Cl, undergoes base-promoted E2 elimination to form a single alkene Y. Under similar reaction conditions X, C6H11Br, affords Y and an isomeric alkene. Catalytic hydrogenation of Y produces methylcyclopentane. W readily undergoes an SN2 reaction with sodium iodide in acetone. X does not undergo a similar SN2 reaction. What are the structures of W and X

Answer 1

Answer:

; The structures of both compounds are shown in the attached image.

Explanation:

First, compound W has the molecular formula C6H11Cl, it is observed that it does not have double bonds. removal of E2 produces compound Y, which is an alkene, which is hydrogenated and produces a methylcyclopentane.

Compound W is an alkyl halide that undergoes an SN1 reaction with sodium iodide in the presence of acetone forming the corresponding iodine compound.

while compound X is a tertiary alkyl halide, it is sterically restricted to undergo SN2 reactions.