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Question

Which of the following halides undergo E2 elimination?

A
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B
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C
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D
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Solution

The correct option is D
E2 elimination occurs through an anti mechanism.
That compound will undergo E2 mechanism in which the leaving group X and H at β position are anti-periplanar.
In A and B, hydrogens present at β positions are anti-periplanar and hence the compounds can undergo E2 mechanism

In D, the cyclohexane will undergo ring flipping in which the bulky group will be in equatorial position and the Br will comes in axial position. Thus, hydrogen present at β position will be in anti-periplanar position. So the compound (D) will also undergo E2 elimination.

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