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

Gabriel Synthesis

Organic Chemistry

26. Amines

Gabriel Synthesis

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3:14 minutes

Problem 48a

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.
(a) allyl bromide → allylamine

Verified step by step guidance

Step 1: Begin by understanding the problem. The goal is to convert allyl bromide (CH2=CH-CH2-Br) into allylamine (CH2=CH-CH2-NH2). This involves replacing the bromine atom with an amine group (-NH2).

Step 2: Choose an appropriate synthesis method. Since the Gabriel synthesis is effective for producing primary amines without altering the carbon chain, it is a suitable choice for this conversion.

Step 3: In the Gabriel synthesis, use potassium phthalimide (C8H5NO2K) to react with allyl bromide. This forms an N-alkylphthalimide intermediate, where the bromine atom is replaced by the phthalimide group.

Step 4: Hydrolyze the N-alkylphthalimide intermediate using a strong base, such as NaOH, or acidic conditions, such as HCl. This step cleaves the phthalimide group and releases the primary amine (allylamine).

Step 5: Verify the product structure. Ensure that the final product is allylamine (CH2=CH-CH2-NH2), with the carbon chain unchanged and the bromine atom replaced by the amine group.

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Key Concepts

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

Amine Synthesis Methods

Amine synthesis methods are various chemical reactions used to produce amines, which are organic compounds derived from ammonia. Key methods include the reduction of azides and nitro compounds, as well as the Gabriel synthesis. Understanding these methods is crucial for determining how to convert specific organic substrates, like allyl bromide, into the desired amine product.

Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, or the loss of oxygen, resulting in the conversion of functional groups. In the context of amine synthesis, reducing agents can convert nitro groups or azides into amines without altering the carbon skeleton. This principle is essential for transforming allyl bromide into allylamine while maintaining the integrity of the carbon chain.

Nitrile Formation and Reduction

The formation of nitriles involves the introduction of a cyano group (-C≡N) into a molecule, which can subsequently be reduced to form primary amines. This process adds a carbon atom to the chain, making it a valuable strategy in amine synthesis. Understanding how to manipulate nitriles is important for achieving specific conversions, such as from allyl bromide to allylamine.