Question

Provide ALL products of the following reaction, including those from rearrangements. Be clear on stereochemistry (dash/wedge; cis/trans). When you are done, indicate how many unique products there are. CH2CH3 He, O CH CH CH ,CH CH CH CH, CH CH heat Br H CH You may choose to shorthand the alkyl groups as below: Me Et Pr Bu iPr Pe heat Br H
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Answer #1

Shown above is a typical E1 elimination reaction.

The Br- leaves in the first step to generate a secondary carbocation, which rearranges into a tertiary carbocation by shift of alkyl group(s) from adjacent carbon atom. Loss of a hydrogen in the final step gives the alkene products shown above.

A total of 8 products are drawn below.

Me Et Me Et Pri iPr Me Et Me Me 〉 + Pr. iPr + Pri Pr IPr . Pe heat iPr . Pe Pe H Pe H H Bu Me Et Me Et Et Bu Pe Bu . Pe Bu+

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