Chapter 16: Q13P (page 817)
The following hydrocarbon has an unusually large dipole moment. Explain how a large dipole moment might arise.

Short Answer

Charge separation (both rings are aromatic)
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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.


Charge separation (both rings are aromatic)
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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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