Question 40

Ionic reactions with organic compounds proceed through: (A) Homolytic bond cleavage (B) Heterolytic bond cleavage (C) Free radical formation (D) Primary free radical (E) Secondary free radical. Choose the correct answer from the options given below:

We need to identify the mechanism through which ionic reactions with organic compounds proceed. Heterolytic bond cleavage involves the breaking of a covalent bond such that both shared electrons go to one atom, forming a cation and an anion: $$ A:B \rightarrow A^+ + :B^- \quad \text{(or } A:^- + B^+\text{)} $$

In contrast, homolytic bond cleavage assigns one electron to each atom, generating free radicals: $$ A:B \rightarrow A\cdot + B\cdot $$

Ionic reactions involve the formation of ionic intermediates (carbocations, carbanions) and proceed through attack by nucleophiles or electrophiles. This requires heterolytic bond cleavage, where electron pairs move as a unit, creating charged species. Free radical mechanisms (from homolytic cleavage) produce neutral radicals, not ions. Therefore, ionic reactions proceed through heterolytic bond cleavage (B) only.

The correct answer is Option C: (B) only.

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