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)
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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Get started for freeOne 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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