Organic Chemistry (8th Edition)

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

Chapter 16 - Aromatic Compounds - Problems - Page 724: Problem 16-8

Answer

Heptalene: anti-aromatic Azulene: aromatic Pentalene: anti-aromatic

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) Heptalene is anti-aromatic because it has 12 pi electrons which give a whole number when 4n is solved for n. Azulene is aromatic becasue it passes all the tests. Has 10 pi electrons which give a whole number when 4n+2 is solved for n. Pentalene is anti-aromatic because it has 8 pi electrons which give a whole number when 4n is solved for n.
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