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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

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 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.

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

Explain why each compound is aromatic, antiaromatic, or nonaromatic

(a) Isoxazole

(b) 1,3-thiazole

(c) Pyran

(d) Pyrylium ion

(e) γ - pyrone

(f) 1,2-Dihydropyridine

(g)Cytosine

(h)

Borazole, ,is an unusually stable cyclic compound. Propose a structure for borazole, and explain why it is aromatic.
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