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Chapter 16: Q13P (page 817)

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

Ciprofloxacin is a member of the fluoroquinolone class of antibiotics.

(a) Which of its rings are aromatic?

(b) Which nitrogen atoms are basic?

(c) Which protons would you expect to appear between d 6 and d 8 in the proton NMR spectrum?

Question: The benzene ring alters the reactivity of a neighboring group in the benzylic position much as a double bond alters the reactivity of groups in the allylic position.

Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates.

  1. Use resonance forms to show the delocalization (over four carbon atoms) of the positive charge, unpaired electron, and negative charge of the benzyl cation, radical, and anion.
  2. Toulene reacts with bromine in the presence of light to give benzyl bromide. Propose a mechanism for this reaction.

c. Which of the following reactions will have the faster rate and give the better yield? Use a drawing of the transition state to explain your answer.

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

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.

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?
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