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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5: minutes

Problem 30c

Textbook Question

Show how you would accomplish the following synthetic conversions.
(c) pentanoic acid → pentan-1-amine

Verified step by step guidance

Step 1: Convert pentanoic acid to pentanoyl chloride using thionyl chloride (SOCl₂). This reaction replaces the hydroxyl group (-OH) of the carboxylic acid with a chlorine atom, forming an acyl chloride.

Step 2: React pentanoyl chloride with ammonia (NH₃) to form pentanamide. This nucleophilic substitution reaction replaces the chlorine atom with an amide group (-CONH₂).

Step 3: Reduce pentanamide to pentan-1-amine using a reducing agent such as lithium aluminum hydride (LiAlH₄). This reduction converts the amide group (-CONH₂) to an amine group (-CH₂NH₂).

Step 4: Perform a workup step to neutralize the reaction mixture and isolate pentan-1-amine. Typically, this involves adding water or an acid to quench the reducing agent and purify the product.

Step 5: Confirm the structure of pentan-1-amine using spectroscopic techniques such as NMR or IR to ensure the desired product has been synthesized.

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Key Concepts

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

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are known for their acidic properties and can undergo various reactions, including reduction and conversion to amines. In this context, pentanoic acid serves as the starting material for the synthesis of pentan-1-amine.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, carboxylic acids can be reduced to primary alcohols or amines using reducing agents such as lithium aluminum hydride (LiAlH4) or borane (BH3). Understanding the mechanism of these reactions is crucial for converting pentanoic acid to pentan-1-amine.

Amine Synthesis

Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. The synthesis of amines from carboxylic acids typically involves a two-step process: first, reduction to an alcohol, followed by further reduction to the corresponding amine. This transformation is essential for achieving the desired product, pentan-1-amine, from pentanoic acid.

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Related Practice

Textbook Question

How can the following compounds be prepared from the given starting materials?

Textbook Question

Show how each of the following compounds can be prepared, using the given starting material:

Textbook Question

Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.

(a) aniline

Textbook Question

Show how you would accomplish the following synthetic conversions.

(f) (R)-2-bromobutane → (S)-2-methylbutan-1-amine

Textbook Question

Show how you would accomplish the following synthetic conversions.

(b) 1-bromo-2-phenylethane → 3-phenylpropan-1-amine

Textbook Question

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(d) 4-methoxyaniline

Textbook Question

Synthesize from benzene. (Hint: All of these require diazonium ions.)