Question

Consider the following solvents for potential use in a Grignard reaction.

a) Acetone

b) Dioxane

c) Ethanol

For each solvent, indicate (yes or no) whether or not the solvent will be suitable for use in a Grignard reaction. If yes, explain why. If no, explain why not, and draw a balanced reaction scheme for the side reaction (NOT the desired reaction) that will likely occur instead.

Answer 1

Grignard reagent based reactions done in aprotic solvents like THF or diethyl ether.

A. Acetone yes, non protic solvent

B. Dioxane, yes, since it is non protic solvent

C. Ethanol, No since it is protic solvent it releases proton and reacts with Grignard reagent to form alkane/arene.

RMgBr + EtOH---> R-H + Mg(OH)Br