JEE Main · 2026 · 22 Jan 2026 · Shift 1 · Hydrocarbons

In chlorocyclohexane the chlorine is bonded to an $s{p}^3$ carbon and acts only through its electron-withdrawing inductive effect. In chlorobenzene a lone pair on chlorine is delocalised into the aromatic ring. This conjugation gives the C-Cl bond partial double-bond character (statement B holds) and, by feeding electron density back from chlorine, lowers the polarity of the C-Cl bond compared with the purely inductive case in chlorocyclohexane (statement C holds); the ring carbon carrying chlorine is $s{p}^2$ hybridised (statement E holds). The same delocalisation reduces the negative charge on chlorine rather than raising it, and the partial double-bond character shortens the bond rather than lengthening it, so statements A and D are wrong. The statements that apply are B, C and E.