Classify the following compounds as aromatic, antiaromatic, or nonaromatic

(a)

(b)

(c)

(d)

Short Answer

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(a)

(b)

(c)

(d)

Step by step solution

01

Aromaticity

The aromaticity of any planar and nonplanar molecule can be identified by Huckel’s rule, i.e., (4n+2)where n represents the number of pi electrons.

02

Classification of the aromatic and nonaromatic molecule

(a)

The total number of pi electrons in conjugation is 14 which shows that the compound obeys the Huckel rule, i.e., (4n+2)pi electrons. In this case, the value of n is 3. Thus, the given structure is non-aromatic.

(b)

As one of the carbons in the given ring is sp3hybridized, therefore, p orbital is not available for the delocalization of the pi electrons. Hence, the given structure is non-aromatic.

(c)

The total number of pi electrons in conjugation is 14 which shows that the compound obeys the Huckel rule, that is (4n+2)electrons. In this case, the value of n is 3.

The structure is cyclic and planar in nature as all the carbons are sp3hybridized. Thus, the given structure is aromatic.

(d)

The total number of pi electrons in conjugation is 14 which shows that the compound obeys the Huckel rule, that is(4n+2)electrons. In this case, the value of n is 3.

The structure is cyclic and planar in nature as all the carbons are sp2hybridized. Thus, the given structure is aromatic.

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Most popular questions from this chapter

(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

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

(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.)

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(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?

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(c) Methyl pentalene


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