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

Short Answer

Expert verified

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

The polarization of a carbonyl group can be represented by a pair of resonance structures

Cyclopropenone and cycloheptatrienone are more stable than anticipated. Cyclopentadienone, however, is relatively unstable and rapidly undergoes a Diels–Alder dimerization. Explain.

Cyclopropenone CycloheptatrienoneCyclopentadienone

Explain why each compound is aromatic, antiaromatic, or nonaromatic

(a) Isoxazole

(b) 1,3-thiazole

(c) Pyran

(d) Pyrylium ion

(e) γ - pyrone

(f) 1,2-Dihydropyridine

(g)Cytosine

(h)

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.

(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?

(c) Draw resonance forms to show the charge distribution on the pyrrole structure

(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

Question: For each NMR spectrum, propose a structure consistent with the spectrum and the additional information provided.

a. Elemental analysis shows the molecular formula to be C8H7OCl . The IR spectrum shows a moderate absorption at 1602 cm-1 and a strong absorption at 1690 cm-1 .

b.The mass spectrum shows a double molecular ion of ratio 1:1 at m/z 184 and 186.

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