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

Molecular Geometry

Organic Chemistry

1. A Review of General Chemistry

Molecular Geometry

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Problem 51c,d

Textbook Question

What is the hybridization of all the atoms (other than hydrogen) in each of the following?
What are the bond angles around each atom?
c. ^-CH₃
d. ⋅CH₃

Verified step by step guidance

Step 1: Understand the concept of hybridization. Hybridization is the mixing of atomic orbitals to form new hybrid orbitals that are used to form bonds. The type of hybridization depends on the steric number (number of sigma bonds + lone pairs) around the atom.

Step 2: Analyze the structure of -CH3 (methyl anion). The carbon atom in -CH3 has three sigma bonds (to three hydrogen atoms) and one lone pair. Calculate the steric number: 3 sigma bonds + 1 lone pair = 4. A steric number of 4 corresponds to sp³ hybridization. The bond angles around an sp³ hybridized atom are approximately 109.5°.

Step 3: Analyze the structure of ⋅CH3 (methyl radical). The carbon atom in ⋅CH3 has three sigma bonds (to three hydrogen atoms) and one unpaired electron. Calculate the steric number: 3 sigma bonds + 0 lone pairs = 3. A steric number of 3 corresponds to sp² hybridization. The bond angles around an sp² hybridized atom are approximately 120°.

Step 4: Note the difference between the two species. In -CH3, the lone pair on carbon contributes to the steric number, leading to sp³ hybridization. In ⋅CH3, the unpaired electron does not contribute to the steric number, resulting in sp² hybridization.

Step 5: Summarize the findings. For -CH3, the carbon is sp³ hybridized with bond angles of approximately 109.5°. For ⋅CH3, the carbon is sp² hybridized with bond angles of approximately 120°.

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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 of mixing atomic orbitals to form new hybrid orbitals that can accommodate the bonding requirements of an atom. In organic chemistry, common types include sp, sp2, and sp3 hybridization, which correspond to different geometries and bond angles. For example, sp3 hybridization leads to tetrahedral geometry with bond angles of approximately 109.5 degrees.

Bond Angles

Bond angles are the angles formed between two adjacent bonds at a central atom. They are influenced by the hybridization of the atom and the presence of lone pairs, which can repel bonding pairs and alter the ideal angles. Understanding bond angles is crucial for predicting molecular shapes and reactivity in organic compounds.

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. It is determined by the number of bonding pairs and lone pairs around a central atom, which dictate the spatial orientation of the bonds. This concept is essential for understanding the physical and chemical properties of molecules, including their reactivity and interactions.

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Related Practice

Textbook Question

You drew the Lewis structures of the following compounds and ion in Assessment 2.32. Predict their shapes around the central atom based on the Lewis structure.

(d) CO₃^2-

Textbook Question

Predict the approximate size of the following bond angles.

(b) the C—N—C bond angle in a secondary amine

Textbook Question

You drew the Lewis structures of the following compounds and ion in Assessment 2.32. Predict their shapes around the central atom based on the Lewis structure.

Textbook Question

Describe the orbitals used in bonding and the bond angles in the following compounds:

a. CH₃O^-

Textbook Question

For each of the following molecules, indicate the hybridization of each carbon and give the approximate values of all the bond angles:

b. CH₃CH═CH₂

Textbook Question

a. Which of the species have bond angles of 109.5°?

b. Which of the species have bond angles of 120°?

NH₃ ⁺NH₄ ^-CH₃

Textbook Question

Predict the approximate size of the following bond angles.