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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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2:51 minutes

Problem 60f

Textbook Question

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

Verified step by step guidance

Step 1: Begin with cyclohexanone as the starting material. Cyclohexanone is a ketone with the formula C₆H₁₀O. The goal is to convert the ketone group into a primary amine (-CH₂NH₂) attached to the cyclohexane ring.

Step 2: Perform a reductive amination reaction. Reductive amination is a common method to synthesize amines from ketones. First, react cyclohexanone with ammonia (NH₃) to form an imine intermediate. The imine is formed by the nucleophilic attack of ammonia on the carbonyl group of cyclohexanone, followed by the elimination of water.

Step 3: Reduce the imine intermediate to the corresponding amine. Use a reducing agent such as sodium cyanoborohydride (NaBH₃CN) or hydrogen gas (H₂) with a metal catalyst like palladium on carbon (Pd/C). This step converts the imine into the desired primary amine (-CH₂NH₂).

Step 4: Ensure the reaction conditions are mild to prevent over-reduction or side reactions. Sodium cyanoborohydride is often preferred for reductive amination because it selectively reduces imines without affecting other functional groups.

Step 5: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of the compound. Confirm the structure of the product using spectroscopic methods like NMR or IR to ensure the synthesis was successful.

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Key Concepts

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

Cyclohexanone

Cyclohexanone is a cyclic ketone with the formula C6H10O. It serves as a versatile starting material in organic synthesis due to its reactivity, particularly at the carbonyl group. This compound can undergo various reactions, including nucleophilic addition, which is essential for synthesizing amines and other derivatives.

Imine and Enamine Formation

Imine and enamine formation are key reactions involving the condensation of carbonyl compounds with amines. An imine is formed when a primary amine reacts with a carbonyl compound, while an enamine is produced from a secondary amine. Understanding these mechanisms is crucial for synthesizing compounds from cyclohexanone, as they dictate the structure and reactivity of the resulting products.

Nucleophilic Addition Reactions

Nucleophilic addition reactions are fundamental in organic chemistry, where a nucleophile attacks an electrophilic carbon atom, such as the carbonyl carbon in cyclohexanone. This reaction is pivotal for forming new carbon-nitrogen bonds, which are essential in synthesizing amines and other nitrogen-containing compounds from cyclohexanone.

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Related Practice

Textbook Question

Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.

(a) Ph–CH=C(CH₃)₂

(b) Ph–C(CH₃)=CH₂

Textbook Question

Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.

(d)

Textbook Question

Predict the major products of the following reactions.

(h)

Textbook Question

(a) Outline the syntheses indicated in Solved Problem 18-2, beginning with aldehydes and alkyl halides.

(b) Both of these syntheses of 1-phenylbuta-1,3-diene form the central double bond. Show how you would synthesize this target molecule by forming the terminal double bond.

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(f) octanoic acid

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(g) ethyl octanoate

Textbook Question

Show how you would accomplish the following syntheses.

(b) benzonitrile → propiophenone

Textbook Question

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

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

Key Concepts

Cyclohexanone

Imine and Enamine Formation

Nucleophilic Addition Reactions

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