What is the hybridization of the nitrogen atom in the following molecule? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch25_Q03_QT.jpg" alt="The figure illustrates the structure of a molecule. A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 6 is single bonded to C 4 of a 1 N and 4 C heteronuclear alkene chain depicted as a line structure using 4 zigzag lines. N occupies the first position. In the heteronuclear alkene chain, a double bond is present between C 3 and C 4. N is single bonded to H above and H on the lower left. C 2 of the heteronuclear alkene chain is double bonded to O above. C 4 of the heteronuclear alkene chain is single bonded to C H 3 above in the form of a line." />

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 nitrogen atom in the following molecule?

sp³

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

sp²

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Verified step by step guidance

Identify the nitrogen atom in the given molecule. It is the atom bonded to two hydrogen atoms and a carbon atom.

Determine the number of sigma bonds and lone pairs around the nitrogen atom. In this molecule, nitrogen is bonded to two hydrogen atoms and one carbon atom, making a total of three sigma bonds.

Consider the possibility of resonance structures. The nitrogen atom can participate in resonance with the adjacent carbonyl group, which may affect its hybridization.

Evaluate the hybridization state of nitrogen in each resonance structure. In the structure where nitrogen forms three sigma bonds and has one lone pair, it is sp3 hybridized. In the resonance structure where nitrogen is involved in a pi bond with the carbonyl group, it is sp2 hybridized.

Conclude that the nitrogen atom exhibits sp3 hybridization in one resonance contributor and sp2 hybridization in another, due to its involvement in resonance with the carbonyl group.