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

Reductive Amination

Organic Chemistry

26. Amines

Reductive Amination

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2:23 minutes

Problem 42d

Textbook Question

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

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Step 1: Analyze the transformation. The starting material is a cyclic ketone (cyclooctanone), and the product is a cyclic amine (cyclooctylamine). This indicates that the ketone functional group needs to be converted into an amine group.

Step 2: Use reductive amination as the key reaction. Reductive amination involves the reaction of a ketone with ammonia (NH₃) or a primary amine in the presence of a reducing agent to form an amine.

Step 3: Add ammonia (NH₃) to the ketone. This will form an imine intermediate through a condensation reaction where water is eliminated. The imine has the general structure R₂C=NH.

Step 4: Reduce the imine intermediate to the amine. Use a reducing agent such as sodium cyanoborohydride (NaBH₃CN) or hydrogen gas (H₂) with a metal catalyst (e.g., Pd/C) to selectively reduce the imine to the amine without affecting other parts of the molecule.

Step 5: Confirm the product structure. The final product should be cyclooctylamine, where the ketone group has been successfully replaced with an amine group.

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Key Concepts

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

Organic Synthesis

Organic synthesis is the process of constructing organic compounds through chemical reactions. It involves the strategic selection of reagents and conditions to achieve desired transformations. Understanding the principles of synthesis is crucial for designing pathways that lead to specific products, often requiring knowledge of functional groups and reaction mechanisms.

Reagents and Reaction Conditions

Reagents are substances used to bring about a chemical reaction, while reaction conditions refer to the specific environment in which the reaction occurs, including temperature, pressure, and solvent. Selecting appropriate reagents and optimizing conditions is essential for successful synthesis, as they can significantly influence the yield and purity of the desired product.

Mechanisms of Organic Reactions

The mechanism of an organic reaction describes the step-by-step sequence of events that occur during the transformation of reactants into products. Understanding mechanisms helps predict the outcomes of reactions, including the formation of intermediates and the stereochemistry of products. This knowledge is vital for planning synthetic routes and troubleshooting unexpected results.

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Related Practice

Textbook Question

Propose mechanisms for the following reactions.

(a)

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(a) benzylmethylamine from benzaldehyde

(b) N-benzylpiperidine from piperidine

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(f)

Textbook Question

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

Textbook Question

Predict the products of the following reactions:

(h)

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(e)

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

(a) reductive amination (3 ways).

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

Key Concepts

Organic Synthesis

Reagents and Reaction Conditions

Mechanisms of Organic Reactions

Watch next

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