Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
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Chapter 18, Problem 42PP
Interpretation Introduction

Interpretation: For the given cation, using Frost circle an energy diagram should be drawn and it should be predicted whether this cation exhibit aromatic stabilization or not

Concept introduction:

  • The conditions for aromatic compound are,
    1. 1. It should be planar
    2. 2. It must obey the Huckel’s rule

The requirement of an odd number of electron pair is called Huckel’s rule. A     compound can only be aromatic if the number of π electron in the ring is 2, 6,10,14,18 and so on. This series of number can be expressed mathematically as 4n+2 , where n should be an integer and the compound is aromatic.

  1. 3. Continuous conjugated π system(all carbon should be in sp2 hybridized state)

If any compound which doesn’t satisfy one of the above condition then the compound is not aromatic

  • A five membered ring will be aromatic if it contains six π electrons. In order to have six π electrons, one of the carbon atoms must possess two electrons. It should be a carbanion.
  • A Frost circle is used to draw an energy diagram showing the relative energy levels of the molecular orbitals associated with ring comprised of a continuous conjugated π system

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