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Explain why the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
ChemistryHaloalkanes and HaloarenesNEET
Options:
  • A In chlorobenzene, the Cl-atom is linked to a sp2hybridized carbon atom.In cyclohexyl chloride,the Cl-atom is linked to a sp3hybridized carbon atom. Now, the sp2hybridized carbon has more s-character than the sp3hybridized carbon atom.Moreover, the R effect of the benzene ring of chlorobenzene decreases the electron density of the C−Cl bond near the Cl-atom.Hence, the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
  • B Chlorobenzene has a greater electron density around the chlorine atom due to resonance, reducing the overall dipole moment.
  • C Chlorobenzene has a smaller molecular mass compared to cyclohexyl chloride, resulting in a lower dipole moment.
  • D Chlorobenzene forms a stronger hydrogen bond with itself, reducing its overall dipole moment compared to cyclohexyl chloride.
Solution:
1430 Upvotes Verified Answer
The correct answer is: In chlorobenzene, the Cl-atom is linked to a sp2hybridized carbon atom.In cyclohexyl chloride,the Cl-atom is linked to a sp3hybridized carbon atom. Now, the sp2hybridized carbon has more s-character than the sp3hybridized carbon atom.Moreover, the R effect of the benzene ring of chlorobenzene decreases the electron density of the C−Cl bond near the Cl-atom.Hence, the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
Correct Option is : (A)
In chlorobenzene, the Cl-atom is linked to a sp2hybridized carbon atom.In cyclohexyl chloride,the Cl-atom is linked to a sp3hybridized carbon atom. Now, the sp2hybridized carbon has more s-character than the sp3hybridized carbon atom.Moreover, the R effect of the benzene ring of chlorobenzene decreases the electron density of the C−Cl bond near the Cl-atom.Hence, the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.

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