Q21P - 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 yields phenyl magnesium bromide. But when treated with CO₂, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound which on hydrolysis with aqueous acid produces 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 ether yields  2-butylmagnesium bromide. But when treated with CO₂, will add  to nucleophile of Grignard reagent . It leads to the production of intermediate compound which on hydrolysis with aqueous acid yields Butanoic acid.

The reaction mechanism can be denoted as,

Step 3: Production prediction and mechanism for (c)

When Bromo cyclopropane treated with Mg in dry ether can yield the propyl magnesium bromide. But when treated with CO₂, will add to nucleophile of Grignard reagent  of  carbonyl carbon. It also leads to the production of intermediate compound which on hydrolysis with aqueous acid yields Cyclopropane carboxylic acid.

The reaction mechanism can be denoted as,