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Question

The major product of the following reaction when heated is:


A

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B

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C

Both products are nearly in equal proportions

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D

None of the above

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Solution

The correct option is A


Given a choice, hydrogen is abstracted instead of deuterium because the CH bond is weaker.
For E2, we need carbon-hydrogen and the carbon-bromine bonds to be anti-periplanar.
They should be coplanar but the CBr and CH bonds should be on opposite sides.

After rotation, the antiperiplanar structure is in place for E2 (major product is):


For the minor product (only 17% yield), DBr is eliminated as:


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