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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 CH 3 − Cl .
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii)S N 1 reactions are accompanied by racemization in optically active alkyl halides.
(i)
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii)
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 s p 2 hybridized carbon, it has less tendency to release electrons than the s p 3 hybrid of C − Cl (in cyclohexyl chloride). Hence, chlorobenzene is more electronegative resulting in decrease in polarity of C − Cl bond.
(ii) The dipole moment of chlorobenzene is lower as bond length is shorter
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