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

Previous problemNext problem

2:26 minutes

Problem 84d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the starting material and the product. The starting material is a cyclic amide (lactam) with a ketone group, and the product is a cyclic amine. This suggests a reduction reaction to convert the amide to an amine.

Step 2: Identify the appropriate reducing agent. Common reducing agents for amides include lithium aluminum hydride (LiAlH4), which is highly effective for reducing amides to amines.

Step 3: Set up the reaction conditions. Dissolve the starting material in a dry solvent such as tetrahydrofuran (THF) and add LiAlH4 slowly under controlled conditions to avoid side reactions.

Step 4: Allow the reaction to proceed. The LiAlH4 will reduce the carbonyl group of the amide to form the corresponding amine. Monitor the reaction progress using techniques like thin-layer chromatography (TLC).

Step 5: Work up the reaction. Quench the reaction by carefully adding water or an acidic solution to destroy excess LiAlH4, then isolate the product by extraction and purification methods such as recrystallization or column chromatography.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of carbonyl groups (C=O) to alcohols (C-OH) or amines (C-NH2). The reaction shown in the image depicts the reduction of an imine or a similar nitrogen-containing compound, which is a common transformation in organic synthesis.

Amine Chemistry

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles in various reactions, including reductions. Understanding the structure and reactivity of amines is crucial for predicting the outcomes of reactions involving nitrogen-containing compounds, such as the one illustrated in the image.

Mechanism of Reduction

The mechanism of reduction typically involves the transfer of hydride ions (H-) or the addition of hydrogen gas (H2) to the substrate. In the case of the reaction shown, a reducing agent such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) may be used to facilitate the conversion of the carbonyl or imine to the corresponding amine. Understanding these mechanisms is essential for predicting reaction pathways and products.

Watch next

Master The Primary Amines Flowchart with a bite sized video explanation from Johnny

Start learning