Q21E - Organic Chemistry (Mcmurry)

Question

Predict the product and provide the mechanism for each reaction below.

Step-by-Step Solution

Answer

The product prediction and its mechanism for each of the reaction can be explained.

Step 1: Production prediction and mechanism for (a)

When bromobenzene treated with Mg in dry can yield the phenylmagnesium bromide. But treated with CO₂, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product is Benzoic acid.

The formation mechanism can be denoted as,

Step 2: Production prediction and mechanism for (b)

When 2-bromobutane treated with Mg in dry can yield the 2-butylmagnesium bromide. But treated with CO₂, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product is Butanoic acid.

The formation mechanism can be denoted as,

Step 3: Production prediction and mechanism for (c)

When bromocyclopropane treated with Mg in dry can yield the propylmagnesium bromide. But treated with CO₂, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product is Cyclopropanecarboxylic acid.

The formation mechanism can be denoted as,