Answer to Question #220663 in Organic Chemistry for Arslan

Question

What product(s) would be formed when
organomagnesium reacts with carbonyl compounds,
cyanogen chloride, halogenated compounds and alkyl
chloroformate ? Explain with mechanism in each case.

Answer 1

In a grignard reaction,alkyl or alyl magnesium halide is alcohol to a carbonyl group in an aldihyde or ketone .

this reaction helps in the formation of carbon carbon bond .

Therefore when phenyl magnesium bromide reacts with dimethyl carbo nate ,then following reaction takes place.

Major organic products are- (a) propan-1-ol and (b) 2-methylpropan-2-ol

Explanation:

methyl magnesium bromide gives nucleophilic addition reaction with carbonyl group. Because methyl magnesium bromide is a strong nucleophile and carbonyl group is a strong electrophilic center.

Propanal contains an aldehyde group and propanone contains a ketone group. hence they both give nucleophilic addition with methyl magnesium bromide.

Dilute acid is added to protonate the alkoxide produced during nucleophilic addition.

Reactions are shown below.