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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

When 3-chlorocyclopropene is treated with AgBF4, AgCl precipitates. The organic product can be obtained as a crystalline material, soluble in polar solvents such as nitromethane but insoluble in hexane. When the crystalline material is dissolved in nitromethane containing KCl, the original 3-chlorocyclopropene is regenerated. Determine the structure of the crystalline material, and write equations for its formation and its reaction with chloride ion

The proton NMR spectrum of 2-pyridone gives the chemical shifts shown.

(a) Is 2-pyridone aromatic?

(b) Use resonance forms to explain your answer to (a). Also explain why the protons at d 7.31 and d 7.26 are more deshielded than the other two (d 6.15 and d 6.57).

(c) Thymine is one of the heterocyclic bases found in DNA. Do you expect thymine to be aromatic? Explain.

(d) The structure of 5-fluorouracil is shown in the box at the side of the page. Is 5-fluorouracil aromatic? Explain.

(a) Draw the molecular orbitals for the cyclopropenyl case. H H H (Because there are three p orbitals, there must be three MOs: one all-bonding MO and one degenerate pair of MOs.)

(b) Draw an energy diagram for the cyclopropenyl MOs. (The polygon rule is helpful.) Label each MO as bonding, nonbonding, or antibonding, and add the nonbonding line. Notice that it goes through the approximate average of the MOs.

(c) Add electrons to your energy diagram to show the configuration of the cyclopropenyl cation and the cyclopropenyl anion. Which is aromatic and which is antiaromatic?

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.

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
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