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Chapter 16: 16-8P (page 812)

One of the following compounds is much more stable than the other two. Classify each as aromatic, antiaromatic, or nonaromatic

(a)Methyl heptalene

(b) Methyl azulene


(c) Methyl pentalene


Short Answer

Expert verified

(a) Methyl heptalene


(b) Methyl azulene


(c) Methyl pentalene


Step by step solution

01

Aromaticity

Enrich Huckel demonstrated a rule which predicts that the given annulene or related compounds are aromatic or antiaromatic. If the number of electrons in a pi-electron system is (4n+2), the system is aromatic and if it is 4n then the system is antiaromatic where n is an integer.

02

Classification of the aromatic and nonaromatic molecule

Heptalene is antiaromatic, azulene is aromatic because it follows pi electrons and it is planar. Pentalene is antiaromatic. Azulene is aromatic, hence it is most stable than the other two which are antiaromatic.

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Most popular questions from this chapter

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

Repeat Problem 16-10 for the cyclopentadienyl ions.

(a) Draw one all-bonding MO, then a pair of degenerate MOs, and then a final pair of degenerate MOs.

(b)Draw the energy diagram, fill in the electrons, and confirm the electronic configurations of the cyclopentadienyl cation and anion.

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

(a) Use the polygon rule to draw an energy diagram for the MOs of a planar cyclooctatetraenyl system.

(b) Fill in the eight pi electrons for cyclooctatetraene. Is this electronic configuration aromatic or antiaromatic? Could the cyclooctatetraene system be aromatic if it gained or lost electrons?

(c) Draw pictorial representations for the three bonding MOs and the two nonbonding MOs of cyclooctatetraene. The antibonding MOs are difficult to draw, except for the all-antibonding MO

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

(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
See all solutions

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