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CBSE Class 12 Chemistry 2016 Delhi Set 1 Solved Paper

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Question : 11 of 26
Marks: +1, -0
Give reasons:
(i) CCl\mathrm{C}-\mathrm{Cl} bond length in chlorobenzene is shorter than CCl\mathrm{C}-\mathrm{Cl} bond length in CH3Cl\mathrm{CH}_3-\mathrm{Cl}.
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii) SN1\mathrm{S}_{\mathrm{N}}1 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)(\mu = q \times d) due to resonance and sp2\mathrm{sp}^2 hybridized carbon, it has less tendency to release electrons than the sp3\mathrm{sp}^3 hybrid of CCl\mathrm{C}-\mathrm{Cl} (in cyclohexyl chloride). Hence, chlorobenzene is more electronegative resulting in decrease in polarity of CCl\mathrm{C}-\mathrm{Cl} bond.
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