Q51 E - Organic Chemistry (Mcmurry)

Question

21-51 What product would you expect to obtain from Grignard reaction of an excess of phenylmagnesium bromide with dimethyl carbonate, $C{H}_{3}OC{O}_{2}C{H}_3$ ?

Step-by-Step Solution

Answer

The Grignard reaction involved reaction is given as, 

The end product is  , which is diphenyl methanol with phenyl as one of the alkyl groups.

Introduction to the Concept

A chemical compound's structural formula is a graphic depiction of the molecular structure (derived by structural chemistry methods) that shows how the atoms might be organised in real three-dimensional space.

Solution Explanation

Because the Grignard reagent is in excess, two sequential Grignard additions occur at the carbonyl carbon of dimethyl carbonate.

Mechanistically,

Because it is a weak leaving group, the second molecule of the Grignard reagent adds to the total reduction.

The dimethyl ketone is converted to alcohol with two identical Ph substituents by excessive nucleophilic addition and reduction by the Grignard reagent.