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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6:06 minutes

Problem 54f

Textbook Question

Predict the hybridization and geometry of the carbon and nitrogen atoms in the following molecules and ions. (Hint: Resonance.)
f.

Verified step by step guidance

Identify the structure of the molecule: The given structure is a five-membered ring with an oxygen atom, a nitrogen atom, and a positive charge on the oxygen. This is a pyrrole-like structure with an additional oxygen atom.

Determine the hybridization of the carbon atoms: In a five-membered ring with alternating double bonds, the carbon atoms are typically sp² hybridized. This allows for the formation of a planar structure with 120-degree bond angles.

Analyze the nitrogen atom: The nitrogen atom in this structure is bonded to two carbon atoms and one hydrogen atom, and it has a lone pair. In pyrrole, the nitrogen is sp² hybridized, allowing the lone pair to participate in resonance with the π system of the ring.

Consider the oxygen atom: The oxygen atom has a positive charge, indicating it is likely involved in resonance. Typically, oxygen in such structures is sp² hybridized, allowing for resonance stabilization of the positive charge.

Conclude the geometry: The sp² hybridization of the carbon and nitrogen atoms suggests a planar geometry for the ring, with bond angles close to 120 degrees. The resonance in the ring stabilizes the structure, allowing for delocalization of electrons.

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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 process of mixing atomic orbitals to form new hybrid orbitals, which can explain the geometry and bonding properties of molecules. For carbon and nitrogen atoms, common hybridizations include sp3, sp2, and sp, corresponding to tetrahedral, trigonal planar, and linear geometries, respectively. Determining hybridization involves counting the number of sigma bonds and lone pairs around the atom.

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. It is influenced by the hybridization of the central atom and the presence of lone pairs. For example, sp3 hybridization typically results in a tetrahedral shape, while sp2 leads to a trigonal planar geometry. Understanding geometry is crucial for predicting molecular behavior and reactivity.

Resonance

Resonance describes the delocalization of electrons across multiple structures, which stabilizes the molecule. It involves drawing resonance structures that depict different possible arrangements of electrons, particularly pi electrons and lone pairs. In the given molecule, resonance can affect the hybridization and geometry of the nitrogen atom, as it shares electrons with adjacent atoms, influencing its bonding and structure.

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Predict the hybridization and geometry of the carbon and nitrogen atoms in the following molecules and ions. (Hint: Resonance.)f.

Key Concepts

Hybridization

Molecular Geometry

Resonance

Watch next

Predict the hybridization and geometry of the carbon and nitrogen atoms in the following molecules and ions. (Hint: Resonance.)
f.