Chapter 8, Problem 70PP

Interpretation Introduction

Interpretation:

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

Concept introduction:

Tertiary substrates and strong bases favor bimolecular reaction. Sodium ethoxide can act as a bulky strong nucleophile as well as a strong base. S_N² and E2 are two bimolecular reactions. They are concerted (one step) reactions.

In S_N² 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.

To draw: the transition state of the reaction between $\text{tert-butyl chloride}$ and sodium hydroxide.