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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Problem 8a,b,c

Textbook Question

What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
a.
b.
c.

Verified step by step guidance

Identify the highlighted carbons in the structure. In the first image, the highlighted carbons are part of a single bond (σ bond) between two sp3 hybridized carbons. In the second image, the highlighted carbons are part of a double bond (σ and π bonds) between an sp2 hybridized carbon and an sp3 hybridized carbon. In the third image, the highlighted carbons are part of a triple bond (σ and two π bonds) between two sp hybridized carbons.

Understand the hybridization of the carbons involved. Hybridization determines the type of orbitals used in bonding. For sp3 hybridized carbons, the σ bond is formed using sp3 orbitals. For sp2 hybridized carbons, the σ bond is formed using sp2 orbitals, and the π bond is formed using unhybridized p orbitals. For sp hybridized carbons, the σ bond is formed using sp orbitals, and the π bonds are formed using unhybridized p orbitals.

Analyze the bonding in the first image. The carbon-carbon σ bond is formed by the overlap of two sp3 orbitals, as both carbons are sp3 hybridized.

Analyze the bonding in the second image. The carbon-carbon σ bond is formed by the overlap of an sp2 orbital from one carbon and an sp3 orbital from the other carbon. The π bond is formed by the side-by-side overlap of unhybridized p orbitals from the sp2 hybridized carbon.

Analyze the bonding in the third image. The carbon-carbon σ bond is formed by the overlap of two sp orbitals, and the two π bonds are formed by the side-by-side overlap of unhybridized p orbitals from each sp hybridized carbon.

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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 by which atomic orbitals mix to form new hybrid orbitals that are suitable for the pairing of electrons to form chemical bonds. In carbon, the most common hybridizations are sp3, sp2, and sp, which correspond to different types of bonding and molecular geometries. Understanding hybridization is crucial for determining the types of bonds formed between carbon atoms.

Sigma Bonds

A sigma (σ) bond is a type of covalent bond formed by the head-on overlap of atomic orbitals. In the case of carbon–carbon bonds, the overlap can occur between hybrid orbitals (like sp3 or sp2) or between an s orbital and a hybrid orbital. Sigma bonds are characterized by their cylindrical symmetry around the bond axis and are the first bonds formed between two atoms.

Orbital Overlap

Orbital overlap refers to the extent to which atomic orbitals from two atoms share the same space when forming a bond. The greater the overlap, the stronger the bond. In carbon–carbon bonds, understanding how the specific orbitals overlap (such as s, p, or hybrid orbitals) is essential for predicting bond strength and molecular structure.

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Related Practice

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

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

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

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?

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What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?a. b. c.

Key Concepts

Hybridization

Sigma Bonds

Orbital Overlap

Watch next

What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
a.
b.
c.