Question

Draw the products of homolysis or heterolysis of each indicated bond. Use electronegativity differences to decide on the location of charges in the heterolysis reaction. Classify each carbon reactive intermediate as a radical, carbocation, or carbanion.

a.

b.

Short answer

Answer

a. A radical intermediate is generated.

b. A carbocation intermediate is generated.

Step-by-step solution

Step-by-Step SolutionStep 1: Homolysis and Heterolysis

The cleavage of a bond in which each atom involved in the bonding retains one electron is termed homolytic cleavage or homolysis.

The cleavage of a bond in which both the electrons involved in bonding are transferred to one of the atoms (the more electronegative atom) is termed heterolytic cleavage or heterolysis.

Carbon intermediates

The intermediate involving a carbon atom bearing a positive charge (indicating deficiency of electrons) are termed carbocations. The ones bearing a negative charge (indicating an excess of electrons) are termed carbanions.

The carbon species having an unshared electron over them are termed carbon radicals.

Products of the given bond cleavage

a.

Homolysis of the C-H bond

The homolytic cleavage of the bond between the carbon and the hydrogen atom generates a carbon radical as both the carbon and the hydrogen atom get one electron each.

b.Heterolysis of the C-O bond

In the given case, the shared pair of electrons are transferred to the electronegative oxygen atom, and hence a carbocation is generated.