1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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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2:32 minutes

Problem 15.38cBruice - 8th Edition

Textbook Question

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

c. benzylamine

Verified step by step guidance

Identify the structure of benzylamine, which is C6H5CH2NH2.

Understand that in Gabriel synthesis, the phthalimide ion acts as a nucleophile to substitute the halide in an alkyl halide.

Recognize that the alkyl bromide needed should have the structure C6H5CH2Br, which is benzyl bromide.

Consider the mechanism: the phthalimide ion will attack the carbon attached to the bromine in benzyl bromide, displacing the bromide ion.

After the substitution, hydrolysis or hydrazinolysis will release the primary amine, benzylamine, from the phthalimide derivative.

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Key Concepts

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

Gabriel Synthesis

Gabriel synthesis is a method for preparing primary amines from alkyl halides using phthalimide as a nucleophile. The reaction involves the nucleophilic substitution of the alkyl halide with the phthalimide, followed by hydrolysis to yield the amine. This method is particularly useful because it avoids the formation of secondary or tertiary amines, allowing for the selective synthesis of primary amines.

Alkyl Bromides

Alkyl bromides are organic compounds containing a bromine atom attached to an alkyl group. They are commonly used as electrophiles in nucleophilic substitution reactions, such as those in Gabriel synthesis. The choice of alkyl bromide is crucial, as it determines the structure of the resulting amine; for benzylamine, a suitable alkyl bromide would be benzyl bromide, which has a phenyl group attached to the carbon bearing the bromine.

Benzylamine Structure

Benzylamine is an aromatic amine with the structure C6H5CH2NH2, consisting of a benzene ring attached to a -CH2- group, which is further connected to an amino group (-NH2). Understanding its structure is essential for determining the appropriate alkyl bromide for its synthesis. In the context of Gabriel synthesis, the alkyl bromide must provide the benzyl group, making benzyl bromide the ideal choice for producing benzylamine.