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Chapter 16: 16-5P (page 809)

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

Short Answer

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It is a qualitative tool that is represented in the form of a diagram that explains the molecular orbital theory in which bonding in molecules takes place in a linear combination of atomic orbitals.

Step by step solution

01

Molecular orbital diagram

It is a qualitative tool that is represented in the form of a diagram that explains the molecular orbital theory in which bonding in molecules takes place in a linear combination of atomic orbitals.

02

MO energy diagram

The cyclooctatetraene molecule has 8 pi electrons. Of which six are paired but two electrons are unpaired in nonbonding orbitals due to which the configuration of cyclooctatetraene is unstable. The MO diagram of cyclooctatetraene can be represented as follows:

MO energy diagram of cyclooctatetraene

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Most popular questions from this chapter

(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?

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鈥揂lder dimerization. Explain.

Cyclopropenone CycloheptatrienoneCyclopentadienone

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

Show which of the nitrogen atoms in purine are basic, and which one is not basic. For the nonbasic nitrogen, explain why its nonbonding electrons are not easily available to become protonated

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.
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