Chapter 9.2, Problem 5P

(a)

Interpretation Introduction

Interpretation:

The major product of the given reaction has to be given.

Concept introduction:

${\text{S}}_{\text{N}}\text{1}$reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction called unimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}\text{1}$ reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergo ${\text{S}}_{\text{N}}\text{1}$ substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product of the given reaction has to be given.

Concept introduction:

${\text{S}}_{\text{N}}\text{1}$reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction called unimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}\text{1}$ reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes ${\text{S}}_{\text{N}}\text{1}$ substitution reaction.