The following hydrocarbon has an unusually large dipole moment. Explain how a large dipole moment might arise.

Short Answer

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Charge separation (both rings are aromatic)

Step by step solution

01

Step 1:Charge separation

The given hydrocarbon is aromatic. One ring will getpositive and the other negatively charged. Due to charge separation between oppositely charged rings; the large dipole moment arises. Both rings are aromatic because both have 6 pi electrons and hence follows Huckel rule 4n+2 pi electrons where n is

02

 Step 2: Explanation regarding dipole moment

In this, the positive ring compound is an aromatic tropylium ion with 6 pi electrons. In this case, there are several resonances, forms that delocalize the positive charge around the seven-membered ring.

In the case of the negative ring compound which is an aromatic cyclopentadienyl anion with 6 pi electrons, In this case, there are several resonance forms that delocalize the negative charge around the five-membered ring.

Positive and negative charge delocalization

Both rings are aromatic with charge separation

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Most popular questions from this chapter

One of the following compounds is much more stable than the other two. Classify each as aromatic, antiaromatic, or nonaromatic

(a)Methyl heptalene

(b) Methyl azulene


(c) Methyl pentalene


Repeat Problem 16-10 for the cyclopentadienyl ions.

(a) Draw one all-bonding MO, then a pair of degenerate MOs, and then a final pair of degenerate MOs.

(b)Draw the energy diagram, fill in the electrons, and confirm the electronic configurations of the cyclopentadienyl cation and anion.

(c) Add electrons to your energy diagram to show the configuration of the cyclopentadienyl cation and the cyclopentadienyl anion. Which is aromatic and which is antiaromatic?

Does the MO energy diagram of cyclooctatetraene appear to be a particularly stable or unstable configuration? Explain

(a) Use the polygon rule to draw an energy diagram for the MOs of a planar cyclooctatetraenyl system.

(b) Fill in the eight pi electrons for cyclooctatetraene. Is this electronic configuration aromatic or antiaromatic? Could the cyclooctatetraene system be aromatic if it gained or lost electrons?

(c) Draw pictorial representations for the three bonding MOs and the two nonbonding MOs of cyclooctatetraene. The antibonding MOs are difficult to draw, except for the all-antibonding MO


(a) Draw all the Kekulé structures of anthracene and phenanthrene.

(b) Propose mechanisms for the two additions shown.

(c) In Chapter 8, most of the additions of bromine to double bonds gave entirely anti stereochemistry. Explain why the addition to phenanthrene gives a mixture of syn andanti stereochemistry.

(d) When the product from (c) is heated, HBr is evolved, and 9-bromophenanthrene results. Propose a mechanism for this dehydrohalogenation.

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