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1. Is the molecule below aromatic? If so, circle the atoms that are part of the aromaticity. Also indicate the orbital that each lone pair occupies. .N. H2N

1. Is the molecule below aromatic? If so, circle the atoms that are part of the aromaticity. Also indicate the orbital that each lone pair occupies. .N. H2N

Introductory Chemistry: An Active Learning Approach
Introductory Chemistry: An Active Learning Approach
6th Edition
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Mark S. Cracolice, Ed Peters
Chapter22: Biochemistry
Section: Chapter Questions
Problem 22.4TC
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**Question:** Is the molecule below aromatic? If so, circle the atoms that are part of the aromaticity. Also indicate the orbital that each lone pair occupies. **Molecular Structure:** The diagram shows a six-membered aromatic ring (pyridone) with alternating double bonds. There is an amino group (NH₂) attached to the second carbon, and an oxo group (O) double-bonded to the fourth carbon. A nitrogen is part of the ring at the sixth position (next to the oxo group) with a single hydrogen attached, and there is a carbon attached to this nitrogen outside the ring with a terminal methyl group. **Analysis:** - **Aromaticity Check:** The molecule is aromatic. It has a conjugated ring system with alternating single and double bonds, fulfilling Huckel's rule for aromaticity (\(4n + 2\) \( \pi \) electrons; \(n = 1\) gives 6 \( \pi \) electrons). - **Lone Pairs:** - The lone pair on the nitrogen in the ring occupies a \( p \)-orbital, contributing to the aromaticity. - The lone pair on the amino group nitrogen is not involved in the ring’s aromaticity and typically occupies an \( sp^2 \)-hybridized orbital. - The oxygen in the oxo group likely has lone pairs, but they do not contribute to the aromaticity of the ring since the oxygen is double-bonded outside the aromatic system.
Transcribed Image Text:**Question:** Is the molecule below aromatic? If so, circle the atoms that are part of the aromaticity. Also indicate the orbital that each lone pair occupies. **Molecular Structure:** The diagram shows a six-membered aromatic ring (pyridone) with alternating double bonds. There is an amino group (NH₂) attached to the second carbon, and an oxo group (O) double-bonded to the fourth carbon. A nitrogen is part of the ring at the sixth position (next to the oxo group) with a single hydrogen attached, and there is a carbon attached to this nitrogen outside the ring with a terminal methyl group. **Analysis:** - **Aromaticity Check:** The molecule is aromatic. It has a conjugated ring system with alternating single and double bonds, fulfilling Huckel's rule for aromaticity (\(4n + 2\) \( \pi \) electrons; \(n = 1\) gives 6 \( \pi \) electrons). - **Lone Pairs:** - The lone pair on the nitrogen in the ring occupies a \( p \)-orbital, contributing to the aromaticity. - The lone pair on the amino group nitrogen is not involved in the ring’s aromaticity and typically occupies an \( sp^2 \)-hybridized orbital. - The oxygen in the oxo group likely has lone pairs, but they do not contribute to the aromaticity of the ring since the oxygen is double-bonded outside the aromatic system.
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