EBK GET READY FOR ORGANIC CHEMISTRY
EBK GET READY FOR ORGANIC CHEMISTRY
2nd Edition
ISBN: 9780321830555
Author: KARTY
Publisher: VST
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Chapter 14, Problem 14.19P
Interpretation Introduction

Interpretation:

The given compound is aromatic, antiaromatic, or nonaromatic is to be predicted.

Concept introduction:

Heterocyclic compounds are defined as cyclic compounds which contain at least one ring heteroatom. Heterocyclic compounds can be aromatic, nonaromatic, or antiaromatic. In some of the heterocyclic compounds, the heteroatom contributes a p atomic orbital to the aromatic π system. Thus, a heteroatom can contribute a lone pair of electrons to the π system to attain aromaticity. In some cases, this may involve a change in the hybridization of the heteroatom from sp3 to sp2 in spite of the angle strain.

According to Huckel’s rules for aromaticity, a species must possess a fully conjugated π system around the ring. The molecule must be planar, which also means all the ring atoms must be sp2 hybridized. The number of electrons in the π system must be (4n + 2), n = 0, 1, 2, ...

If the number of electrons in the π system is 4n, n = 0, 1, 2, ..., the compound is antiaromatic.

All other compounds are nonaromatic.

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