Problem: How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (e) 2-Bromo-3-methylpentane. 

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We’re being asked to draw the products for the E2 reaction of 2-bromo-3-methylpentane.



Recall that the E2 reaction involves a backside β-elimination from the base:



Because of the concerted mechanism, E2 requires that the β-hydrogen and leaving group are antiperiplanar with each other.


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Problem Details

How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (e) 2-Bromo-3-methylpentane.

 

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.