Q.34. Question: Hydrocarbon A possesse... [FREE SOLUTION]

Chapter 17: Q.34. (page 641)

Question: Hydrocarbon A possesses a significant dipole, even though it is composed of only C-C and C-H bonds. Explain why the dipole arises and use resonance structures to illustrate the direction of the dipole. Which ring is more electron rich?

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Answer

This molecule also possesses a net dipole moment. The seven membered ring is electron deficient and the five-membered ring is electron rich in nature as shown in the structure below:

Resonating structures

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Aromatic compounds

The compounds which are cyclic, are planar, and have a total of $(4 n + 2) 蟺$ electrons are aromatic in nature. The aromatic compounds are stable than the acyclic compounds with similar number of $蟺$ electrons.

The most common aromatic compound is benzene.

The illustration of the dipole in the given molecule.

For the given compound, the following resonating structures are possible:

Resonating structures

From the above resonating structures, it is clear that there is a negative charge on the five membered ring. It also shows that there is a positive charge on the seven-membered ring.

The above resonating structure also makes it clear that each ring has a total of $6 蟺$ electrons which makes it aromatic in nature. This molecule also possesses a net dipole moment. The seven membered ring is electron deficient and the five-membered ring is electron rich in nature.