JEE MainChemistryGeneral Organic Chemistry
Identify the compound that possesses the highest dipole moment among the following.
Options
- A2,4,6 -Cycloheptatrien- 1 -one
- BCyclopentadienone
- C1,4 -Benzoquinone
- D2 -Cyclohexen- 1 -one
Correct answer
A. 2,4,6 -Cycloheptatrien- 1 -one
Step-by-step solution
The dipole moment of a cyclic ketone depends on the contribution of its polarized resonance structure ( C ^+- O ^- ). In 2,4,6 -cycloheptatrien- 1 -one (tropone), polarization of the carbonyl group generates a positive charge on the seven-membered ring. This forms the cycloheptatrienyl cation (tropylium ion), which has 6 electrons and is highly stable due to aromaticity. This dominant resonance contributor results in a very high dipole moment. In cyclopentadienone, polarization would create a cyclopentadienyl catio