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

Reductive Amination

Organic Chemistry

26. Amines

Reductive Amination

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4:17 minutes

Problem 35b

Textbook Question

The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
b.

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Step 1: Identify the amino acid structure shown in the image. The compound has an amino group (-NH2) attached to the α-carbon, a carboxylate group (-COO⁻), and a benzyl side chain (a phenyl group attached to a CH2 group). This structure corresponds to the amino acid phenylalanine.

Step 2: Recall the Strecker synthesis, a common method for synthesizing α-amino acids. In this method, an aldehyde reacts with ammonia and hydrogen cyanide to form an α-aminonitrile, which is then hydrolyzed to yield the α-amino acid.

Step 3: Determine the carbonyl compound needed for the synthesis. The side chain of phenylalanine (a benzyl group) suggests that the starting carbonyl compound should be benzaldehyde (C6H5CHO), which has a phenyl group directly attached to the aldehyde functional group.

Step 4: Write the reaction sequence. Benzaldehyde reacts with ammonia (NH3) and hydrogen cyanide (HCN) to form phenylaminonitrile. This intermediate is then hydrolyzed under acidic or basic conditions to yield phenylalanine.

Step 5: Summarize the synthesis. The carbonyl compound required to synthesize phenylalanine is benzaldehyde. This compound undergoes the Strecker synthesis to produce the desired amino acid.

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Key Concepts

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

Amino Acids

Amino acids are organic compounds that serve as the building blocks of proteins. They contain both an amine group (-NH2) and a carboxylic acid group (-COOH), making them α-aminocarboxylic acids. The structure of amino acids allows them to participate in various biochemical reactions, including protein synthesis and enzyme activity.

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbonyl group (C=O), which is a carbon atom double-bonded to an oxygen atom. They are classified into aldehydes and ketones, depending on the position of the carbonyl group. In the synthesis of amino acids, carbonyl compounds can react with amines to form amino acids through processes such as reductive amination.

Synthesis of Amino Acids

The synthesis of amino acids often involves the reaction of carbonyl compounds with amines. This can occur through various methods, including the Strecker synthesis and Gabriel synthesis. Understanding the specific carbonyl compounds needed for synthesizing particular amino acids is crucial for organic synthesis and biochemistry, as it allows for the production of these essential biomolecules.

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Related Practice

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.

(d) cyclohexanone → N-cyclohexylpyrrolidine

Textbook Question

What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?

Multiple Choice

Which of the following will NOT successfully synthesize valine?

Textbook Question

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

Textbook Question

The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?

Textbook Question

Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?

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.

(b) benzaldehyde → benzylamine

Textbook Question

Propose mechanisms for the following reactions.

(a)

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