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JEE Main levelSingle correct optionDifficulty 2 of 3hx152

The dipole moment of $CH X_{3} Cl$ is about 1.9 D whereas that of $C X_{6} H X_{5} Cl$ is about 1.7 D. The best explanation is that in chlorobenzene

Athe benzene ring withdraws electrons from chlorine by the $- R$ effect
Bchlorine is less electronegative than in chloromethane
Cthe $C - Cl$ bond is longer than in chloromethane
Dthe $+ R$ donation of chlorine's lone pair into the ring and the greater electronegativity of $s p^{2}$ carbon both reduce the polarity of the $C - Cl$ bond

Answer: D

In chlorobenzene the

s p^{2}

carbon is more electronegative than the

s p^{3}

carbon of

CH X_{3} Cl

, so the charge separation is smaller, and chlorine pushes some electron density into the ring by resonance, opposing the bond dipole. The

C - Cl

bond is shorter, not longer.

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