Q.61 - Organic Chemistry

Question

Draw a stepwise, detailed mechanism for the following reaction.

Step-by-Step Solution

Answer

The mechanism for the formation of the substitution and elimination products are shown below:

Types of reactions

Weak bases and weak nucleophiles such as water promote a mixture of both  ${\mathbf{\text{S}}}_{\mathbf{\text{N}}}\mathbf{\text{1}}$ and E1 reactions. Here water is used, which acts both as a weak base and weak nucleophile. As a result, they give a mixture of both ${\text{S}}_{\text{N}}\text{1}$  and E1 reactions.

Types of reactions by tertiary halides

Tertiary halides undergo a  ${\text{S}}_{\text{N}}\text{1}$ and E1 reaction respectively when a weak nucleophile and a weak base are used, such as water which is so observed in this reaction.

Similarities in both the reaction pathway

Both  ${\text{S}}_{\text{N}}\text{1}$ and E1 reactions are two-step processes, and carbocation formation is the rate-determining step.

 

By considering all the steps, the mechanism for the formation of the substitution and elimination products are shown below:

Representation of the detailed reaction schemes