Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 21, Problem 43P

Open the molecular model file for benzyne and examine the following molecular orbitals: the LUMO (lowest unoccupied molecular orbital), the HOMO (highest occupied molecular orbital), the HOMO-1 (next lower energy orbital), the HOMO-2 (next lower in energy), and the HOMO-3 (next lower in energy).

(a) Which orbital best represents the region where electrons of the additional π bond in benzyne would be found?

(b) Which orbital would accept electrons from a Lewis base on nucleophilic addition to benzyne?

(c) Which orbitals are associated with the six πelectrons of the aromatic system? Recall that each molecular orbital can hold a maximum of two electrons.

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