Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 28P
Interpretation Introduction

Interpretation:

The aromaticity of cyclononatetraenyl anion and the dianion formed by [16] annulene is to be explained.

Concept introduction:

In accordance with the Huckel’s rule, aromatic compounds contain a planar ring and have a conjugated pi system with (4n+2)π electrons, where n=0,1,2,3,...

Aromatic compounds contain conjugated pi bonds.

All the atoms in the aromatic ring have an unhybridized p orbital.

Compounds that are planar, cyclic and having conjugated pi system, with (4n)π electrons are antiaromatic. They are highly unstable.

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Consider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?
Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?
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Chapter 14 Solutions

Organic Chemistry

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