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

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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1:22 minutes

Problem 37b

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:
1. Free-radical chain reaction
2. Reaction involving strong bases and strong nucleophiles
3. Reaction involving strong acids and strong electrophiles
(b)

Verified step by step guidance

Identify the type of reaction: The reaction involves an acid (H+) and water (H2O), which suggests an acid-catalyzed hydration mechanism.

Analyze the starting material: The starting compound is a cyclic ketone with an alkene group, indicating that the reaction may involve the addition of water across the double bond.

Protonation step: The acid (H+) will protonate the alkene, forming a more stable carbocation intermediate. This step is crucial as it activates the alkene for nucleophilic attack.

Nucleophilic attack: Water (H2O) acts as a nucleophile and attacks the carbocation, leading to the formation of an oxonium ion intermediate.

Deprotonation step: The oxonium ion is deprotonated by another water molecule, resulting in the formation of the final diol product, where two hydroxyl groups are added to the original alkene positions.

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Key Concepts

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

Free-Radical Chain Reactions

Free-radical chain reactions involve a series of steps where free radicals are generated and react with stable molecules, leading to the formation of new radicals. These reactions typically include initiation, propagation, and termination phases. They are common in processes like polymerization and combustion, where the presence of heat or light can initiate the reaction.

Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. Strong bases often act as nucleophiles, attacking electrophilic centers in molecules. Understanding the reactivity of these species is crucial for predicting the outcome of organic reactions, such as substitution and addition mechanisms.

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of acids to increase the rate of a reaction by protonating a reactant, making it more electrophilic. This mechanism is common in hydration reactions, where water adds to alkenes or carbonyl compounds. The presence of a strong acid facilitates the formation of carbocations, which are key intermediates in many organic transformations.

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Related Practice

Textbook Question

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(e) CH₃CH₂OH

Textbook Question

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(f) (CH₃)₂S

Textbook Question

Which atoms in the enol ether would you expect to react with Br⁺ ?

Textbook Question

To which atom of formaldehyde would you expect H⁺ to add?

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(a)

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles.

(d)

Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(c)

Textbook Question

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

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For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect: 1. Free-radical chain reaction 2. Reaction involving strong bases and strong nucleophiles 3. Reaction involving strong acids and strong electrophiles(b)

Key Concepts

Free-Radical Chain Reactions

Nucleophiles and Electrophiles

Acid-Catalyzed Reactions

Watch next

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:
1. Free-radical chain reaction
2. Reaction involving strong bases and strong nucleophiles
3. Reaction involving strong acids and strong electrophiles
(b)