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Achiral compound X has the formula C8H17Br. Y, C8H17Cl, is chiral. X undergoes base-promoted E2 elimination...

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.

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