Haloalkanes and Haloarenes Part 2

Concept:In chlorobenzene, chlorine shows both $-\mathrm{I}$ (inductive withdrawal) and $+\mathrm{M}$ (resonance donation) effects. The $+\mathrm{M}$ effect reduces polarity and gives the $\mathrm{C}$–$\mathrm{Cl}$ bond partial double bond character. The carbon is $\mathrm{sp}^2$ hybridized.Explanation:In chlorocyclohexane, chlorine only shows $-\mathrm{I}$ effect; the $\mathrm{C}$–$\mathrm{Cl}$ bond is a normal single bond, more polar.In chlorobenzene, the $+\mathrm{M}$ effect partly neutralises the $-\mathrm{I}$ effect, making the bond less polar than in chlorocyclohexane.Resonance delocalises chlorine lone pairs into the ring, so the $\mathrm{C}$–$\mathrm{Cl}$ bond gains partial double bond character (statement B is correct).Due to this partial double bond, the bond is shorter, not longer (statement D is false).The negative charge on chlorine is less in chlorobenzene because lone pairs are donated to the ring (statement A is false).The carbon in the benzene ring is $\mathrm{sp}^2$ hybridised, so the $\mathrm{C}$–$\mathrm{Cl}$ bond uses an $\mathrm{sp}^2$ orbital (statement E is correct).Thus, correct statements are B, C, and E.Answer:A. B, C and E Only