Question

Draw a stepwise detailed mechanism that illustrates how four organic products are formed in the following reaction.

Short answer

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

The carbocation formation is stable here, and the resonance condition is also present. As a result, different kinds of elimination and substitution products are formed.

Step-by-step solution

Types of bases or nucleophiles used

Weak bases and weak nucleophiles such as methanol 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 role="math" localid="1649226552056" ${\text{S}}_{\text{N}}\text{1}$ and E1 reactions.

Types of substrates used

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 observed in this reaction.

Similarities in both the reaction pathway

Both ${\text{S}}_{\text{N}}\text{1}$ and E1 reaction is a two-step process, 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:-

Different kinds of products are formed due to the delocalization of pi-electrons inside the 6-membered ring.

Representation of the detailed reaction scheme