Chapter 6, Problem 33P

Interpretation Introduction

Interpretation:

The reagents that are the more reactive nucleophile in a polar aprotic solvent from the given listed pairs are to be determined.

Concept introduction:

An ${\text{S}}_{\text{N}}\text{2}$ reaction is the nucleophilic substitution reaction in which two components are involved in the rate determining step.

The ${\text{S}}_{\text{N}}\text{2}$ reaction is favored by a polar aprotic solvent.

Examples of polar aprotic solvents are acetone, HMPA, DMF, and DMSO.

Nucleophilicity is the phenomena of measuring the ability of any nucleophile to react with an electron deficient species.

Nucleophiles are Lewis bases, mean electron rich and have the ability to donate electron pairs.

The order of nucleophilicity can be decided on the basis of charge.

A negatively charged nucleophile is more reactive than its conjugate acid.

In the given nucleophiles, the negatively charged nucleophiles are more reactive than the neutral one.

The nucleophile attached with electron withdrawing group has less nucleophilicity because electron withdrawing attracts electron density toward itself.

Protic solvents are the solvents that form hydrogen bonds. They contain a hydrogen atom, which is bonded to an electronegative atom such as oxygen or nitrogen.

Aprotic solvents are the solvents that do not form hydrogen bonds.