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Questions
Give reasons:
The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
Explain why the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
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Solution
- To understand the lower dipole moment of chlorobenzene, we must examine the contributing structures of the molecules.
- The C–Cl bond in chlorobenzene exhibits partial double-bond character (structures II, III, and IV). As a result, the C–Cl bond length is shorter than a single bond but longer than a double bond.
- The positive charge on the Cl atom minimises the expected negative (δ−) charge due to electronegativity.
- As a result, the dipole moment is determined by bond length and the partial negative charge on the Cl atom, which decreases. However, this does not occur with cyclohexyl chloride. The carbon in this alkyl halide is purely sp3 hybridised, with a bond length of a single bond and a greater dipole moment due to the presence of (δ−) on Cl.
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