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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3:19 minutes

Problem 54h

Textbook Question

What are the products of the following reactions?
h.

Verified step by step guidance

Step 1: Identify the functional group in the reactant. The reactant contains a nitrile group (-C≡N), which is a carbon triple-bonded to a nitrogen atom.

Step 2: Recognize the reaction conditions. The presence of hydrogen gas (H₂) and Raney nickel indicates a catalytic hydrogenation reaction.

Step 3: Understand the mechanism of catalytic hydrogenation. Under these conditions, the nitrile group undergoes reduction, where the triple bond is broken, and hydrogen atoms are added to form an amine group (-CH₂-NH₂).

Step 4: Analyze the structure of the product. The cyclohexane ring remains intact, and the nitrile group is converted into a primary amine (-CH₂-NH₂).

Step 5: Write the final product structure. The product is cyclohexylamine, which has the formula C₆H₁₁-NH₂.

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Key Concepts

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

Alkynes

Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are unsaturated compounds and are generally more reactive than alkenes and alkanes due to the presence of the triple bond. In organic reactions, alkynes can undergo various transformations, including hydrogenation, where they react with hydrogen to form alkenes or alkanes.

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to a compound, typically in the presence of a catalyst. This process is commonly used to convert unsaturated hydrocarbons, such as alkynes and alkenes, into saturated hydrocarbons. The catalyst, such as Raney nickel, facilitates the reaction by lowering the activation energy required for the hydrogen to add across the multiple bonds.

Raney Nickel Catalyst

Raney nickel is a finely divided nickel-aluminum alloy that serves as a catalyst in hydrogenation reactions. It is particularly effective for reducing alkynes and alkenes to alkanes. The high surface area of Raney nickel enhances its catalytic activity, allowing for efficient hydrogenation under mild conditions, making it a valuable tool in organic synthesis.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide → benzylamine

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

Predict the products of the following reactions:

(k)

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.

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What are the products of the following reactions?h.

Key Concepts

Alkynes

Hydrogenation

Raney Nickel Catalyst

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What are the products of the following reactions?
h.