Chapter 7, Problem 66PP

Interpretation Introduction

Interpretation:

The transition state of the reaction between $\text{tert-butyl chloride}$ and sodium hydroxide should be drawn.

Concept Introduction:

${\text{S}}_{\text{N}}2$Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction.

Leaving group: it is a fragment that leaves substrate with a pair of electrons via heterolytic bond cleavage.

Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of chemical bond.

Tertiary substrates and strong bases favor bimolecular reaction. Sodium ethoxide can act as a bulky strong nucleophile as well as a strong base. ${\text{S}}_{\text{N}}2$ and $E2$ are two bimolecular reactions. They are concerted (one step) reactions.

In ${\text{S}}_{\text{N}}2$ reaction, nucleophile cannot approach a tertiary alkyl halide because of the high steric hindrance.

In $E2$ reaction, strong base can abstract the β-proton of a tertiary alkyl halide.

Transition state is a state in between the reactant and product.

In the transition state of $E2$ reaction: the abstraction of β-proton by the base, removal of leaving group (halo-group) and formation of double bond are taking place.