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

3. Acids and Bases

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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Problem 49a

Textbook Question

For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(a)

Verified step by step guidance

Step 1: Analyze the reactants and products. The reactants are acetic acid (CH3COOH) and isopropyl bromide ((CH3)2CHBr). The products are isopropyl acetate (CH3COOCH(CH3)2) and HBr.

Step 2: Identify the bonds broken in the reaction. In acetic acid, the O-H σ bond is broken. In isopropyl bromide, the C-Br σ bond is broken.

Step 3: Identify the bonds formed in the reaction. A new C-O σ bond is formed between the carbonyl oxygen of acetic acid and the isopropyl group. Additionally, an H-Br σ bond is formed.

Step 4: Classify the bonds broken and formed. Both the bonds broken (O-H and C-Br) and the bonds formed (C-O and H-Br) are σ bonds. No π bonds are involved in this reaction.

Step 5: Summarize the reaction mechanism. This is an example of a nucleophilic acyl substitution reaction, where the nucleophile (isopropyl group) replaces the hydroxyl group of acetic acid, forming an ester and HBr as byproducts.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Types of Chemical Bonds

In organic chemistry, bonds between atoms can be classified as sigma (σ) or pi (π) bonds. Sigma bonds are formed by the head-on overlap of atomic orbitals and are the first bonds formed between two atoms. Pi bonds, on the other hand, result from the side-to-side overlap of p orbitals and are typically found in double and triple bonds. Understanding these bond types is crucial for analyzing reactions.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants are converted into products. It includes the breaking and forming of bonds, which can involve the movement of electrons. Identifying the specific bonds broken and formed during a reaction helps in understanding the mechanism and predicting the outcome of the reaction.

Nucleophiles and Electrophiles

In organic reactions, nucleophiles are species that donate an electron pair to form a bond, while electrophiles are electron-deficient species that accept an electron pair. In the given reaction, the hydroxyl group (OH) acts as a nucleophile, attacking the electrophilic carbon in the alkyl bromide. Recognizing these roles is essential for determining which bonds are broken and formed during the reaction.

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Related Practice

Textbook Question

Specify which in each pair is the harder Lewis acid. Justify your choice beyond just looking at Table 20.2.

(a) Al³⁺ vs. B³⁺

Textbook Question

Suggest an arrow-pushing mechanism for each of the following acid–base reactions.

(d) [an intramolecular reaction]

Textbook Question

Draw two important resonance structures involving the C―O π bond for the molecule shown. To which carbons would you expect a nucleophile to add?

Textbook Question

Suggest an arrow-pushing mechanism that accounts for the formation of the following Lewis acid–Lewis base complexes. Label the Lewis acid and Lewis base in each.

(a)

Textbook Question

One of the more reactive species we will study in organic chemistry is the carbene (molecular formula of CH₂). The carbene can react as both a Lewis acid and a Lewis base. Explain these properties.

Textbook Question

Suggest an arrow-pushing mechanism that accounts for the formation of the following Lewis acid–Lewis base complexes. Label the Lewis acid and Lewis base in each.

(b)

Textbook Question

In comparison to CH₃⁺ in Assessment 2.82, the related molecule H₃O⁺ is not a Lewis acid at oxygen. Why?

Textbook Question

In Chapter 4, we explain that molecules like CH₃^- are Lewis bases or electron pair donors. What makes it a Lewis base?

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For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.(a)

Key Concepts

Types of Chemical Bonds

Reaction Mechanisms

Nucleophiles and Electrophiles

Watch next

For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(a)