What is the hybridization of the indicated nitrogen atom? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch19_Q04_QT.jpg" alt="The figure illustrates the structure of a molecule. A 5-membered heterocyclic pentagonal ring is in a vertical orientation and consists of 1 N and 4 C atoms. N occupies the first position, which is the top right vertex. N is single bonded to a central C atom in the form of a line. The central C atom is double bonded to O above and single bonded to C H 3 on the lower right in the form of a line. An arrow points to the N atom." />

sp 3 in this resonance contributor, but sp 2 in the other resonance contributor.

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1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

1. A Review of General Chemistry

Hybridization

Organic Chemistry

1. A Review of General Chemistry

Hybridization

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Multiple Choice

What is the hybridization of the indicated nitrogen atom?

sp³ in this resonance contributor, but sp² in the other resonance contributor.

sp²

sp³

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Verified step by step guidance

Identify the nitrogen atom in the structure and note its connectivity. The nitrogen is bonded to two carbon atoms and has a lone pair of electrons.

Consider the resonance structures of the molecule. The lone pair on the nitrogen can participate in resonance with the adjacent carbonyl group, forming a double bond between nitrogen and the carbonyl carbon.

In the resonance structure where the nitrogen forms a double bond, the nitrogen atom is involved in a pi bond, which requires p orbitals. This suggests sp2 hybridization.

In the original structure without resonance, the nitrogen is bonded to three groups (two carbons and a lone pair), which typically suggests sp3 hybridization.

Conclude that the nitrogen atom exhibits sp2 hybridization in the resonance structure where it participates in pi bonding, and sp3 hybridization in the structure where it does not participate in resonance.