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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

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

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

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 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

Question: For each NMR spectrum, propose a structure consistent with the spectrum and the additional information provided.

a. Elemental analysis shows the molecular formula to be C8H7OCl . The IR spectrum shows a moderate absorption at 1602 cm-1 and a strong absorption at 1690 cm-1 .

b. The mass spectrum shows a double molecular ion of ratio 1:1 at m/z 184 and 186.

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