Steric demands of the leaving group

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Steric demands of the leaving group

1. If the steric demands of the leaving group in the 2-methyl-s-butyl system were greater than those of a methyl group, why would 2-methyl-1-butene be expected to be formed in greater amounts than if the leaving group were smaller than methyl, regardless of which base is used? Use Newman projections to support your explanation.

2. It has been shown that there is an important stereoelectronic requirement for an anti-periplanar relationship between the leaving group and the beta-hydrogen during an E2 elimination. Predict the structure of the man product of the dehydrobromination of trans-2-bromomethylcyclohesane using alcoholic potassium hydroxide. (Hint: the elimination may not occur via the lowest energy chair conformer.)

 

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