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Chapter 16: 16-6P (page 811)

Make a model of cyclooctatetraene in the tub conformation. Draw this conformation, and estimate the angle between the p orbitals of adjacent pi bonds

Short Answer

Expert verified

It is a type of stereoisomerism in which isomers are interconverted by rotation around formally single bonds. Cyclooctatetraene is a non-planar molecule and in a normal state, it adopts a tub confirmation.

Step by step solution

01

Conformational isomerism

It is a type of stereoisomerism in which isomers are interconverted by rotation around formally single bonds. Cyclooctatetraene is a non-planar molecule and in a normal state, it adopts a tub confirmation.

02

Representation of tub confirmation of cyclooctatetraene

The given structure suggests the angles between p orbitals on the adjacent pi bond approach90o. The given structure is represented as follows:

Tub confirmation of cyclooctatetraene

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Most popular questions from this chapter


(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?

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

(a)Cyclopnonatetraene cation

(b) Cyclononatetraene anion

(c) [16] annulene dianion

(d) [18] annulene dianion

(e)

(f) [20] annulene dication

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

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.

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.
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