Having a hard time understand why Oxirene is categorized as antiaromatic. It says 4 pi electrons, but I count 3 pairs, the double bond and the 2 lone pairs. can someone explain

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.16P: Which of the molecules and ions given in Problem 21.15 are aromatic according to the Hckel criteria?...
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Having a hard time understand why Oxirene is categorized as antiaromatic. It says 4 pi electrons, but I count 3 pairs, the double bond and the 2 lone pairs. can someone explain

Cyclopropenium cation
(2 pi electrons)
antibonding
bonding
Predicted to be aromatic
Oxirene
(4 pi electrons)
7+ antibonding
*
bonding
Predicted to be antiaromatic
(oxirene has never been
isolated)
Transcribed Image Text:Cyclopropenium cation (2 pi electrons) antibonding bonding Predicted to be aromatic Oxirene (4 pi electrons) 7+ antibonding * bonding Predicted to be antiaromatic (oxirene has never been isolated)
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