Chapter 8, Problem 8.31P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed ${\text{S}}_{\text{N}}\text{1}$ mechanism for the given reaction is to be drawn.

Concept introduction:

A unimolecular nucleophilic substitution ${\text{S}}_{\text{N}}\text{1}$ reaction consists of two steps. First, the leaving group leaves in a heterolysis step yielding a carbocation intermediate. The nucleophile attacks the carbocation in a coordination step. Leaving groups are typically conjugate bases of strong acids. A nucleophile has an atom that carries a full negative charge or a partial negative charge. The charge is necessary for it to be attracted to an atom bearing a positive charge. The atom with the negative charge on the nucleophile has a pair of electrons that can be used to form a bond to an atom in the substrate.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed ${\text{S}}_{\text{N}}\text{1}$ mechanism for the given reaction is to be drawn.

Concept introduction:

A unimolecular nucleophilic substitution ${\text{S}}_{\text{N}}\text{1}$ reaction, with an uncharged nucleophile, consists of three steps. First, the leaving group leaves in a heterolysis step yielding a carbocation intermediate. The nucleophile attacks the carbocation in the coordination step. A proton transfer takes place in the third step to form an uncharged product of the reaction. The leaving group is the group that is broken from the substrate. Leaving groups are typically conjugate bases of strong acids. A nucleophile is the species that reacts with the substrate. A nucleophile has an atom that carries a full negative charge or a partial negative charge.