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

Amines by Reduction

Organic Chemistry

26. Amines

Amines by Reduction

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1:57 minutes

Problem 38k

Textbook Question

Predict the products of the following reactions:
(k)

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Step 1: Identify the functional group in the starting material. The molecule contains a cyclic imine group (C=N) with a methyl substituent attached to the nitrogen atom.

Step 2: Recognize the reagents used in the reaction. Lithium aluminum hydride (LiAlH₄) is a strong reducing agent, and water (H₂O) is used in the second step to quench the reaction.

Step 3: Understand the mechanism of reduction. LiAlH₄ reduces the imine group (C=N) by donating hydride ions (H⁻), converting the imine into an amine (C-NH). The methyl group attached to the nitrogen remains unchanged.

Step 4: Predict the product structure. The cyclic structure remains intact, and the imine group is reduced to a secondary amine (C-NH). The methyl substituent on the nitrogen is preserved.

Step 5: Verify the reaction conditions. Ensure that the reaction proceeds under standard conditions for LiAlH₄ reduction, followed by hydrolysis with water to complete the process and isolate the amine product.

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Key Concepts

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

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often pertains to the conversion of functional groups, such as the reduction of carbonyls or nitro groups to alcohols or amines. In this case, lithium aluminum hydride (LiAlH4) acts as a strong reducing agent, capable of reducing various functional groups, including imines and nitriles.

Lithium Aluminum Hydride (LiAlH4)

LiAlH4 is a powerful reducing agent commonly used in organic synthesis. It can reduce a wide range of functional groups, including esters, carboxylic acids, and amines. When reacting with amines, LiAlH4 can convert imines or nitriles into amines, making it essential for understanding the products of the given reaction. The subsequent addition of water (H2O) is crucial for quenching the reaction and hydrolyzing any remaining LiAlH4.

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of the reaction with LiAlH4, hydrolysis is necessary to neutralize the reducing agent and convert any intermediate products into stable amines. This step is vital for understanding the final products of the reaction, as it ensures that the reaction mixture is safe and that the desired amine is formed.

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Related Practice

Textbook Question

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amine syntheses can be used for the following conversions.

Textbook Question

Starting with cyclohexene, how can the following compounds be prepared?

b. cyclohexylmethylamine

Textbook Question

How could you convert N-methylbenzamide to the following compounds?

a. N-methylbenzylamine

Textbook Question

What are the products of the following reactions?

Textbook Question

Reductive amination of aldehydes and ketones is a versatile method for attaching alkyl groups to amines, but the alkyl group is restricted to a 1° or 2° carbon by this method. Prof. Phil Baran of Scripps Research Institute has reported (Science, 2015, 348 (6237), 886–891) a novel way to reduce an aromatic nitro group and add the resulting amine to an alkene so that the aromatic amine is bonded to a 3° carbon—all in a continuous sequence of reactions.

For example:

Predict the products using these starting materials, all of which are reported in this paper.

(c)

(d)

Textbook Question

Predict the products of the following reactions:

(d)

Textbook Question

The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides. Show how these techniques can be used to accomplish the following syntheses.

Textbook Question

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(b) N-methylbutan-1-amine

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Predict the products of the following reactions:(k)

Key Concepts

Reduction Reactions

Lithium Aluminum Hydride (LiAlH4)

Hydrolysis

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Predict the products of the following reactions:
(k)