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

26. Amines

Hofmann Elimination

Organic Chemistry

26. Amines

Hofmann Elimination

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6:43 minutes

Problem 39j

Textbook Question

Predict the products of the following reactions:
(j)

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Step 1: Analyze the starting material. The given compound is 2-bromopropane, which is a secondary alkyl halide. This will undergo a reaction sequence involving two reagents: trimethylamine ((CH3)3N) and silver oxide (Ag2O) with heat (Δ).

Step 2: Understand the role of trimethylamine ((CH3)3N). Trimethylamine acts as a nucleophile and will likely displace the bromine atom in a nucleophilic substitution reaction, forming an intermediate quaternary ammonium salt.

Step 3: Consider the role of silver oxide (Ag2O) and heat (Δ). Silver oxide in the presence of heat facilitates the Hofmann elimination reaction. This reaction involves the elimination of a β-hydrogen and the leaving group (bromine or the ammonium group), resulting in the formation of an alkene.

Step 4: Determine the regioselectivity of the elimination. The Hofmann elimination typically favors the formation of the less substituted alkene due to steric factors. In this case, the product will likely be propene.

Step 5: Summarize the reaction sequence. The reaction proceeds through nucleophilic substitution to form a quaternary ammonium salt, followed by Hofmann elimination under basic conditions with Ag2O and heat, yielding propene as the final product.

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Key Concepts

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

Hofmann Elimination

Hofmann elimination is a reaction that involves the conversion of a quaternary ammonium salt into an alkene through the elimination of a nitrogen-containing leaving group. This process typically requires a strong base and heat, leading to the formation of an alkene and the release of nitrogen gas. Understanding this mechanism is crucial for predicting the products of the given reaction.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of the provided reaction, the tertiary amine (CH3)3N acts as a nucleophile, attacking the carbon atom bonded to the bromine, which is the leaving group. This step is essential for forming the quaternary ammonium salt necessary for the subsequent elimination.

Silver Oxide (Ag2O) in Organic Reactions

Silver oxide (Ag2O) is often used in organic reactions as a mild oxidizing agent or a source of hydroxide ions. In the context of Hofmann elimination, Ag2O can facilitate the deprotonation of the quaternary ammonium salt, promoting the elimination of the nitrogen leaving group and leading to the formation of the alkene. Recognizing the role of Ag2O is important for understanding the reaction conditions and product formation.

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Related Practice

Textbook Question

What is the major product of each of the following reactions?

b .

Textbook Question

When piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substituted piperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and 3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?

Textbook Question

The following reaction takes place several times faster than the reaction of 2-chlorobutane with HO^-:

a. Explain the enhanced reaction rate.

Textbook Question

Using any necessary reagents, show how you would accomplish the following syntheses.

(c)

Textbook Question

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag₂O, and heating.

(e)

Textbook Question

Predict the products of the following reactions:

(e)

(f)

Textbook Question

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag₂O, and heating.

(a) hexan-2-amine

(b) 2-methylpiperidine

Textbook Question

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofmann product.

(a) Draw the structure of the major (Hofmann) product.

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Predict the products of the following reactions: (j)

Key Concepts

Hofmann Elimination

Nucleophilic Substitution

Silver Oxide (Ag2O) in Organic Reactions

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Predict the products of the following reactions:
(j)