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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3:35 minutes

Problem 60

Textbook Question

Reduction of two different carboxylic acid derivatives with LiAlH₄ would give the amine shown. Identify these carboxylic acid derivatives.

Verified step by step guidance

Understand that LiAlH₄ (Lithium aluminum hydride) is a strong reducing agent commonly used to reduce carboxylic acid derivatives to alcohols or amines.

Recognize that the reduction of carboxylic acid derivatives to amines typically involves the conversion of amides or nitriles.

Consider that amides (RCONH₂) can be reduced by LiAlH₄ to primary amines (RCH₂NH₂).

Consider that nitriles (RCN) can also be reduced by LiAlH₄ to primary amines (RCH₂NH₂).

Identify that the two carboxylic acid derivatives that can be reduced to the same amine are likely an amide and a nitrile, both having the same carbon skeleton as the resulting amine.

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Key Concepts

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

Carboxylic Acid Derivatives

Carboxylic acid derivatives are compounds that can be converted into carboxylic acids through hydrolysis. They include esters, amides, anhydrides, and acyl chlorides. Understanding their reactivity and transformation is crucial for predicting the products of reduction reactions.

Reduction with LiAlH₄

Lithium aluminum hydride (LiAlH₄) is a strong reducing agent used in organic chemistry to convert carboxylic acid derivatives into alcohols or amines. It is particularly effective in reducing esters and amides to primary alcohols and amines, respectively, by breaking the carbon-oxygen or carbon-nitrogen bonds.

Amine Formation

Amines are organic compounds derived from ammonia by replacement of one or more hydrogen atoms with organic groups. In the context of reduction, amines can be formed from amides or nitriles when treated with LiAlH₄, which reduces the carbonyl group to a methylene group, resulting in the formation of primary amines.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions.

(d) pentanoic acid → hexan-1-amine

Textbook Question

Show how you would accomplish the following synthetic conversions.

(e) (R)-2-bromobutane → (S)-butan-2-amine

Textbook Question

Show how you can synthesize the following tertiary amine three different ways, each using a different secondary amine and adding the final substituent by (b) acylation–reduction (3 ways).

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.

(a) benzoic acid → benzylamine

Textbook Question

Predict the product of the following reaction sequences.

(b)

Textbook Question

Give the expected products of lithium aluminum hydride reduction of the following compounds (followed by hydrolysis).

(a) butyronitrile

(b) N-cyclohexylacetamide

Textbook Question

Predict the products of the following reactions.

(e)

(f)