Determine if the compound is aromatic, anti-aromatic, or non-aromatic

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
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## Aromaticity in Organic Compounds

### Task: Determine if the compound is aromatic, anti-aromatic, or non-aromatic

#### Visual Representation:
- The image presents the structure of a five-membered ring containing a sulfur atom with two lone pairs of electrons. The ring also includes alternating double bonds, illustrating a conjugated π-electron system.

#### Detailed Description:
To determine whether the compound is aromatic, anti-aromatic, or non-aromatic, we need to consider several criteria:

1. **Planarity**: The compound must be planar, allowing for continuous overlapping of p-orbitals and hence delocalization of π-electrons.
2. **Conjugation**: The compound should have a fully conjugated π-electron system, meaning every atom in the ring must participate in the π-system by having a p-orbital.
3. **Hückel's Rule**: The molecule must follow Hückel's rule, which states that aromatic compounds must have (4n+2) π-electrons, where n is a non-negative integer (0, 1, 2, ...).

In the given structure:
- The five-membered ring is planar.
- The ring atoms, including sulfur, participate in the conjugated π-system.
- The molecule has a total of 6 π-electrons (4 from the two double bonds and 2 from the sulfur atom).

Using Hückel's rule:
\[ 4n + 2 = 6 \]
\[ 4n = 4 \]
\[ n = 1 \]

Since the compound satisfies all the criteria for aromaticity, it is **aromatic**.
Transcribed Image Text:## Aromaticity in Organic Compounds ### Task: Determine if the compound is aromatic, anti-aromatic, or non-aromatic #### Visual Representation: - The image presents the structure of a five-membered ring containing a sulfur atom with two lone pairs of electrons. The ring also includes alternating double bonds, illustrating a conjugated π-electron system. #### Detailed Description: To determine whether the compound is aromatic, anti-aromatic, or non-aromatic, we need to consider several criteria: 1. **Planarity**: The compound must be planar, allowing for continuous overlapping of p-orbitals and hence delocalization of π-electrons. 2. **Conjugation**: The compound should have a fully conjugated π-electron system, meaning every atom in the ring must participate in the π-system by having a p-orbital. 3. **Hückel's Rule**: The molecule must follow Hückel's rule, which states that aromatic compounds must have (4n+2) π-electrons, where n is a non-negative integer (0, 1, 2, ...). In the given structure: - The five-membered ring is planar. - The ring atoms, including sulfur, participate in the conjugated π-system. - The molecule has a total of 6 π-electrons (4 from the two double bonds and 2 from the sulfur atom). Using Hückel's rule: \[ 4n + 2 = 6 \] \[ 4n = 4 \] \[ n = 1 \] Since the compound satisfies all the criteria for aromaticity, it is **aromatic**.
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