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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2:01 minutes

Problem 11b

Textbook Question

Predict the hybridization of the indicated atoms.
(b)

Verified step by step guidance

Identify the atom in question and examine its bonding environment. Count the number of sigma bonds (single bonds) and lone pairs of electrons around the atom.

Use the formula for hybridization: Hybridization = (Number of sigma bonds + Number of lone pairs). This will help determine the steric number of the atom.

Match the steric number to the corresponding hybridization: steric number 2 = sp, steric number 3 = sp², steric number 4 = sp³, steric number 5 = sp³d, steric number 6 = sp³d².

Consider the geometry of the molecule to confirm the hybridization. For example, sp corresponds to linear geometry, sp² to trigonal planar, and sp³ to tetrahedral.

Verify your prediction by checking the molecular structure and ensuring that the hybridization aligns with the observed bond angles and geometry.

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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 chemistry where atomic orbitals mix to form new hybrid orbitals, which can explain the geometry of molecular bonding. For example, in carbon, the mixing of one s and three p orbitals results in four sp3 hybrid orbitals, leading to a tetrahedral shape. Understanding hybridization helps predict molecular shapes and bond angles.

VSEPR Theory

Valence Shell Electron Pair Repulsion (VSEPR) Theory is used to predict the geometry of molecules based on the repulsion between electron pairs around a central atom. According to VSEPR, electron pairs will arrange themselves to minimize repulsion, leading to specific molecular shapes such as linear, trigonal planar, or tetrahedral. This theory is essential for visualizing molecular structures.

Bonding and Lone Pairs

In molecular structures, bonding pairs of electrons are shared between atoms, while lone pairs are non-bonding electrons localized on a single atom. The presence of lone pairs can significantly affect the hybridization and geometry of a molecule, as they occupy space and influence the arrangement of bonding pairs. Recognizing the role of lone pairs is crucial for accurate predictions of molecular shape.

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Textbook Question

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

Textbook Question

What orbitals contain the electrons represented as lone pairs in the structures of quinoline, indole, imidazole?

Textbook Question

What orbital do the lone-pair electrons occupy in each of the following compounds?

Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

(b) What are the hybridization and shape of the central carbon of CH₂?

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.)

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