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 freeQuestion: 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.
a. 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.
b. 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.
(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
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.
(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.
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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