Question
On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-1-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.
Step 1
First, the pi bond of the vinyl group in vinylcyclohexane attacks the hydrogen atom of HBr, breaking the H-Br bond and forming a new C-H bond. This results in the formation of a secondary allylic carbocation and a bromide ion (Br-). Show more…
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On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-l-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.
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