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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question

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 and Oxirene: Aromatic and Antiaromatic Systems

**Cyclopropenium Cation**

- **Symbol**: A triangle with a positive charge inside.
- **Electron Count**: 2 pi electrons.
- **Molecular Orbital Diagram**: 
  - Two pi electrons fill the lower energy (bonding) molecular orbital.
  - The upper energy (antibonding) orbital remains unoccupied.

**Prediction**: The cyclopropenium cation is predicted to be **aromatic** due to the complete filling of its bonding molecular orbital, following Hückel's rule (4n+2 pi electrons).

---

**Oxirene**

- **Symbol**: A triangle with an oxygen atom at the vertex, displaying two lone pairs.
- **Electron Count**: 4 pi electrons.
- **Molecular Orbital Diagram**: 
  - Four pi electrons partially fill both bonding and antibonding molecular orbitals.

**Prediction**: Oxirene is predicted to be **antiaromatic** based on its electron count and distribution in molecular orbitals. 

*Note*: Oxirene has never been isolated, suggesting its potential instability.
Transcribed Image Text:### Cyclopropenium Cation and Oxirene: Aromatic and Antiaromatic Systems **Cyclopropenium Cation** - **Symbol**: A triangle with a positive charge inside. - **Electron Count**: 2 pi electrons. - **Molecular Orbital Diagram**: - Two pi electrons fill the lower energy (bonding) molecular orbital. - The upper energy (antibonding) orbital remains unoccupied. **Prediction**: The cyclopropenium cation is predicted to be **aromatic** due to the complete filling of its bonding molecular orbital, following Hückel's rule (4n+2 pi electrons). --- **Oxirene** - **Symbol**: A triangle with an oxygen atom at the vertex, displaying two lone pairs. - **Electron Count**: 4 pi electrons. - **Molecular Orbital Diagram**: - Four pi electrons partially fill both bonding and antibonding molecular orbitals. **Prediction**: Oxirene is predicted to be **antiaromatic** based on its electron count and distribution in molecular orbitals. *Note*: Oxirene has never been isolated, suggesting its potential instability.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Electronic Effects
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY