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The C-Cl bond length in chlorobenzene is shorter than C-Cl bond length in CH_(3)-Cl. |
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Answer» Solution :Chlorobenzene can be regarded as a resonance hybrid of FIVE structure. As a RESULT C-CL bond in chlorobenzene has some double bond CHARACTER and hence shorter (169 pm) than C-Cl bond in `CH_(3)-Cl` (177 pm) which has pure single bond character. Alternately, in `CH_(3)-Cl,Cl` is attached to a `sp^(3)`-hybridized carbon while in chlorobenzene it is attached to a `sp^(2)`-hybridized carbon. since a `sp^(2)`-hybridized orbital is smaller in size as compared to a `sp^(3)`-hybridized  ltBrgt orbital of carbon, THEREFORE, `C_Cl` bond in chlorobenzene is shorter (169 pm) than C-Cl bond length in `CH_(3)-Cl` (177 pm).
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