Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 16 - Aromatic Compounds - Problems - Page 729: Problem 16-12 a

Answer

Antiaromatic

Work Step by Step

For compounds to be aromatic they have to pass three tests: 1) Planar- if not planar then they are non- aromatic 2) Hybridization- should be sp/sp$^2$ 3) Huckle's rule- for aromatic 4n+2= # pi electrons (should be a whole number when solved) and for Anti-aromatic 4n = # pi electrons (should be a whole number when solved) It is planar so it passes the 1st test. It has no $sp^3$ carbons so it passes the 2nd test. There are 8 pi electron which is 4n and not a huckel number. Thus, it is antiaromatic.
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