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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2:02 minutes

Problem 37a

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)

Verified step by step guidance

Examine the reactants and products in the given reaction. The reactants are two molecules of acetone (CH₃COCH₃) and the reagent is barium hydroxide (Ba(OH)₂). The product is an aldol condensation product, which is a β-hydroxy ketone.

Recognize that the presence of Ba(OH)₂ suggests a reaction involving a strong base. Barium hydroxide is a strong base that can deprotonate the α-hydrogen of acetone, forming an enolate ion.

Understand the mechanism: The enolate ion formed from acetone acts as a nucleophile and attacks the carbonyl carbon of another acetone molecule, leading to the formation of a new carbon-carbon bond.

Identify the type of reaction: This is an aldol condensation reaction, which typically involves strong bases and nucleophiles. The enolate ion is a strong nucleophile, and the carbonyl carbon is an electrophile.

Classify the reaction: Based on the mechanism and the involvement of strong bases and nucleophiles, this reaction falls under category B: Reaction involving strong bases and strong nucleophiles.

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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 including initiation, propagation, and termination, where free radicals are generated and react with stable molecules. These reactions are characterized by the formation of new radicals that continue the reaction cycle. Common examples include the halogenation of alkanes, where a halogen radical abstracts a hydrogen atom, leading to a chain 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 reactions. Understanding the roles of these species is crucial for predicting reaction mechanisms and outcomes in organic chemistry.

Mechanisms of Organic Reactions

The mechanism of an organic reaction describes the step-by-step process by which reactants are converted into products, detailing the breaking and forming of bonds. Mechanisms can be classified based on the nature of the reactants and the conditions, such as whether they involve ionic or radical pathways. Recognizing these mechanisms helps in understanding reaction conditions and predicting product formation.

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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

(b)

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.

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(a)

Key Concepts

Free-Radical Chain Reactions

Nucleophiles and Electrophiles

Mechanisms of Organic 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
(a)