Chapter 17, Problem 17.52P

Interpretation Introduction

Interpretation:

Why acetone, being an aprotic solvent, cannot be used as a solvent for reactions involving alkyllithium and Grignard reagents is to be explained.

Concept introduction:

Polar protic solvents are capable of hydrogen bonding because they contain at least one hydrogen atom connected directly to an electronegative atom (such as $\text{O-H, or N-H}$). The H atoms is not directly attached to an electronegative atom, and they are unable to form hydrogen bonding is known as polar aprotic solvents. Ketones are considered as aprotic due to the absence of any hydrogen atom directly connected to an electronegative atom. Protic solvents solvate both cations and anions strongly whereas aprotic solvents solvate cations more strongly, but not anions. Grignard reagent and alkyl lithium reagents are used as a source of carbon nucleophiles. These reagents undergo nucleophilic addition reactions to the compounds having a carbonyl group rigorously.