Why dipole moment of cyclopentanone is greater than cyclopentadienone?please help me.

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Jan 9, 2017

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Cyclopentanone

In addition to the bond dipole caused by the C-O electronegativity difference, there is also a resonance contributor

Cyclopentanone

The combination of the two effects gives cyclopentanone a dipole moment of 3.28 D.

Cyclopentadienone

The corresponding resonance contributor in cyclopentadienone is

Cyclopentadienone

In this case, generating a positive charge on the carbonyl carbon generates a highly unstable antiaromatic 4π system.

The relative importance of this contributor will therefore be less, and the dipole moment will be decreased (to 3.13 D).

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