Which of the following compounds will undergo heterolytic cleavage of the C-Br bond most readily?

Step-by-step solution

The ease of heterolytic cleavage of a C-Br bond depends directly on the stability of the carbocation formed after the departure of the bromide ion. Let us analyze the carbocations formed from each compound: 1) Bromobenzene forms a phenyl cation, which is highly unstable as the positive charge resides on an sp^2 hybridized carbon atom. 2) 3-Bromopropene forms an allyl cation ( CH₂=CH-CH₂^+ ), which is a 1^ carbocation stabilized by resonance. 3) 1-Bromo-1-phenylethane forms a 2^ benzylic cation ( C₆H₅-C^+H-CH₃ ). Th