Question

Why is E1 more selective to the Zaitsev product vs the non-zaitsev product? When computing the...

Why is E1 more selective to the Zaitsev product vs the non-zaitsev product? When computing the ratios, it is found that E1 has a higher ratio between the Zaitsev- Non-Zaitsev product. What is the basis of the selectivity. Please give as much detail as possible.

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Answer #1

The E1 reactions proceed by carbocation intermediate. The stability of carbocations is tertiary > secondary > primary and when the beta hydrogen is eliminated , tertiary carbocations usually give more substituted alkenes which are more stable.

Thus in E1 , the most common intermediate is the tertiary carbocation.

And the product is more stable more substituted alkene.

Thus the product stability combined with ease of formation of stable carbocation leads to higher percentage of more substituted alkene which the Zaitsev product.

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