Predict the major alkene product of the following e1 reaction

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Predict the products of the following elimination reaction, and draw the major product formed. Make sure to consider the stereochemistry of the reaction. 3-chloro-3-methylpentane reacts with sodium tertbutoxide in tertbutanol.

Predict the products of the following elimination reaction, and draw the major product formed. Make sure to consider the stereochemistry of the reaction. 3-chloro-3-methylpentane reacts with sodium ethoxide in ethanol.

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Answer:

see explanation below

Explanation:

In the first case, we have a reaction where we have the 3-chloro-3-methylpentane reacting with t-butoxide. The t-butoxide is a very voluminous base, so the strength of substracting a hydrogen atom is reduced. Therefore, the reaction taking place here will be an E2 but instead of substracting the hydrogen from the carbons 2 or 4, it will substract it from the methyl group, cause it has less steric hindrance there and the reaction will go faster.

In the second case, the sodium ethoxide is a strong base, so it will rapidly substract an atom of hydrogen from carbon 2 or 4 to form the (Z) - 3 - methyl - 2- pentene and the substitution product.

Look picture for mechanism and products.


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