CBSE Class 12 Chemistry 2016 Delhi Set 1 Solved Paper

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Question : 11
Total: 26
Give reasons:
(i) C−Cl bond length in chlorobenzene is shorter than C−Cl bond length in CH3−Cl.
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii) SN1 reactions are accompanied by racemization in optically active alkyl halides.
Solution:  
(i) In chlorobenzene, due to resonance, there is a partial double bond character, so bond length is short.
(ii) The dipole moment of chlorobenzene is lower as bond length is shorter (µ=q×d) due to resonance and sp2 hybridized carbon, it has less tendency to release electrons than the sp3 hybrid of C−Cl (in cyclohexyl chloride). Hence, chlorobenzene is more electronegative resulting in decrease in polarity of C−Cl bond.
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