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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4:06 minutes

Problem 54d

Textbook Question

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

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Identify the molecule as pyridine, which is a six-membered aromatic ring containing one nitrogen atom.

Recognize that pyridine is similar to benzene in terms of its aromaticity, with a nitrogen atom replacing one of the CH groups.

Determine the hybridization of the carbon atoms in the ring. Each carbon atom in pyridine is bonded to three other atoms (two carbons and one hydrogen) and participates in a pi bond, indicating sp² hybridization.

Examine the nitrogen atom in pyridine. It is bonded to two carbon atoms and has a lone pair of electrons. The nitrogen atom is also sp² hybridized, with the lone pair occupying an sp² orbital, allowing it to participate in the aromatic pi system.

Conclude that the geometry around each carbon and the nitrogen atom is trigonal planar due to the sp² hybridization, which is consistent with the planar structure of aromatic compounds.

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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 of molecular bonding. In organic chemistry, carbon atoms typically undergo sp3, sp2, or sp hybridization, leading to tetrahedral, trigonal planar, or linear geometries, respectively. For nitrogen in aromatic compounds, sp2 hybridization is common, allowing for planar structures and resonance stabilization.

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. It is determined by the hybridization of the central atom and the repulsion between electron pairs. In the context of aromatic compounds, such as pyridine, the geometry is often trigonal planar due to sp2 hybridization, which allows for resonance and delocalization of electrons across the ring structure.

Resonance

Resonance is a concept used to describe the delocalization of electrons in molecules that cannot be represented by a single Lewis structure. It involves the depiction of multiple contributing structures, which collectively describe the electron distribution. In aromatic compounds, resonance contributes to stability by allowing electrons to be shared across the entire ring, influencing both hybridization and geometry.

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Related Practice

Textbook Question

Predict the hybridization of the indicated atoms.

(b)

Textbook Question

For the following partial structures, the σ bond is shown. Add the indicated number of π bonds, being sure to specify the orientation (that is, x, y, or z axis) of the p orbitals used.

(e)

Textbook Question

Rank C―H σ the following bonds in terms of their bond length. Explain your ranking ( 1= longest ; 3 = shortest).

Textbook Question

What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?

Textbook Question

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

Textbook Question

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

Textbook Question

What orbitals contain the electrons represented as lone pairs in the structures of purine, and pyrimidine?

Textbook Question

Use hybrid orbitals to draw the following molecules.

(a)

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

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.)
d.