Chapter 8, Problem 8.35P

Interpretation Introduction

(a)

Interpretation:

The alkyl halide that can be used to produce the given compound in a ${\text{S}}_{\text{N}}\text{1}$ reaction is to be drawn. Whether the alkyl halide would need to be treated with water or methanol is to be determined, and the corresponding mechanism 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. If the nucleophile is uncharged, then a proton transfer step takes place to get the uncharged product. 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.

Interpretation Introduction

(b)

Interpretation:

The alkyl halide that can be used to produce the given compound in an SN1 reaction is to be drawn. Whether the alkyl halide would need to be treated with water or methanol is to be determined, and the corresponding mechanism 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. If the nucleophile is uncharged, then a proton transfer step takes place to get the uncharged product. 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.