Question

Predict the product (s) and provide the mechanism for each reaction below.

Short answer

Theproducts are,

a) Ammonia and o-methoxyacetophenone.

b) Ammonia and 2,5-dimethylhexan-4-one.

c) Ammonia and cyclopropyl phenyl ketone.

d) Ammonia and 4-ethylhexan-3-one

Step-by-step solution

Production prediction and mechanism for (a)

The Grignard reagent’s nucleophilic addition of methyl magnesium bromide to nitrile group in o-methoxybenzonitrile and protonation of immine anion will give imine formation. The conversion of imine into amino alcohol. The water’s nucleophilic attack follows the transfer of protons. The ammonia loss from amino alcohol in the last step leads to the production of o-methoxyacetophenone. The products are ammonia and o-methoxyacetophenone.

The formation mechanism can be denoted as,

Production prediction and mechanism for (b)

The Grignard reagent’s nucleophilic addition of isopropyl magnesium bromide to nitrile group in 2-methyl butane nitrile and protonation of immine anion will give imine formation. The conversion of imine into amino alcohol. The water’s nucleophilic attack follows the transfer of protons. The ammonia loss from amino alcohol in the last step leads to the production of 2,5-dimethylhexan-4-one. The products are ammonia and 2,5-dimethylhexan-4-one.

The formation mechanism can be denoted as

Production prediction and mechanism for (c)

The Grignard reagent’s nucleophilic addition of phenylmagnesium bromide to nitrile group in cyclopropanenitrile and protonation of immine anion will give imine formation. The conversion of imine into amino alcohol. The water’s nucleophilic attack follows the transfer of protons. The ammonia loss from amino alcohol in the last step leads to the production of cyclopropyl phenyl ketone. The products are ammonia and cyclopropyl phenyl ketone.

The formation mechanism can be denoted as,

Production prediction and mechanism for (d)

The Grignard reagent’s nucleophilic addition of methylmagnesium bromide to nitrile group in 2-ethyl butane nitrile and protonation of immine anion will give imine formation. The conversion of imine into amino alcohol. The water’s nucleophilic attack follows the transfer of protons. The ammonia loss from amino alcohol in the last step leads to the production of 4-ethylhexan-3-one. The products are ammonia and 4-ethylhexan-3-one.

The formation mechanism can be denoted as,