E2 Elimination Reaction of 1-bromo-2-methylbutane

Hard Organic Chemistry Nucleophilic Substitution And Elimination Reactions

Consider the following reaction:

In a laboratory experiment, a chemist is observing the reaction between 1-bromo-2-methylbutane and a hydroxide nucleophile under conditions favoring elimination. Given the structure of 1-bromo-2-methylbutane, which elimination product is most likely to be formed through the E2 mechanism?

2-methyl-1-butene

3-methyl-1-butene

2-methyl-2-butene

1-bromo-2-methylbutane is unreactive in this scenario.

Hint

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