Table of contents

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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4:17 minutes

Problem 53

Textbook Question

Assign the hybridization of the nitrogen in each resonance structure of acetamide.

Verified step by step guidance

Identify the structure of acetamide (CH3CONH2). It consists of a carbonyl group (C=O) attached to a methyl group (CH3) and an amide group (NH2). The nitrogen atom in question is part of the amide group.

Draw all possible resonance structures of acetamide. In one resonance structure, the nitrogen has a lone pair of electrons, and in another, the lone pair is delocalized into the carbonyl group, forming a partial double bond between the nitrogen and the carbonyl carbon.

For the resonance structure where the nitrogen has a lone pair and no delocalization, the nitrogen forms three sigma bonds (one to carbon and two to hydrogen) and has one lone pair. This corresponds to sp³ hybridization because the nitrogen has four regions of electron density (three bonds and one lone pair).

For the resonance structure where the lone pair on nitrogen is delocalized into the carbonyl group, the nitrogen forms two sigma bonds (one to carbon and one to hydrogen) and one pi bond (as part of the delocalized system). This corresponds to sp² hybridization because the nitrogen has three regions of electron density (two sigma bonds and one pi bond).

Conclude that the hybridization of the nitrogen in acetamide depends on the resonance structure: it is sp³ in the structure where the lone pair is localized and sp² in the structure where the lone pair is delocalized into the carbonyl group.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hybridization

Hybridization is the concept in organic chemistry that describes the mixing of atomic orbitals to form new hybrid orbitals. These hybrid orbitals are used to form covalent bonds in molecules. The type of hybridization (e.g., sp, sp2, sp3) depends on the number of electron groups around the atom, influencing the geometry and bonding properties of the molecule.

Resonance Structures

Resonance structures are different Lewis structures for the same molecule that depict the delocalization of electrons. They are used to represent molecules where a single structure cannot adequately describe the electron distribution. The actual structure is a hybrid of these resonance forms, contributing to the stability and reactivity of the molecule.

Acetamide Structure

Acetamide is an amide with the formula CH3CONH2, featuring a carbonyl group (C=O) adjacent to a nitrogen atom. The nitrogen in acetamide can exhibit different hybridization states depending on the resonance structures considered. Understanding the hybridization of nitrogen in these structures is crucial for predicting the molecule's reactivity and properties.

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