Question

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.

Answer 1

When 3-chloro-3-methylpentane reacts with sodium tert-butoxide in tert-butanol, an elimination reaction occurs, resulting in the formation of 3-methyl-3-pentene as the major product.

Step-by-step explanation:

When 3-chloro-3-methylpentane reacts with sodium tert-butoxide in tert-butanol, an elimination reaction occurs. The reaction mechanism is known as E2 (bimolecular elimination).

The elimination reaction involves the loss of a hydrogen atom and a leaving group (chlorine in this case) from adjacent carbon atoms, resulting in the formation of a double bond in the product compound. In this case, the major product formed will be 3-methyl-3-pentene.

It is important to consider the stereochemistry of the reaction. Since the reaction does not involve any chiral centers, the stereochemistry of the reactant does not affect the stereochemistry of the product.

Answer 2

see explanation below

Step-by-step 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.