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

Nitrogenous Nucleophiles

Organic Chemistry

26. Amines

Nitrogenous Nucleophiles

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2:05 minutes

Problem 68

Textbook Question

The synthesis of ⍺-hydroxy acids can be done starting with amino acids. Suggest a mechanism of the two-step transformation shown. [The alcohol oxygen is the same in the reactant and product.

Verified step by step guidance

Step 1: Begin by examining the starting material, which is an amino acid with a carboxylic acid group, an amino group, and an alcohol group. The target molecule is an ⍺-hydroxy acid with a cyano group replacing the amino group.

Step 2: The first step involves the use of NaNO₂ and HCl. This combination is typically used for diazotization, where the amino group is converted into a diazonium salt. The diazonium salt is a key intermediate that can undergo various transformations.

Step 3: In the second step, NaCN is introduced. The diazonium salt can be displaced by a nucleophile, such as cyanide ion (CN⁻), resulting in the formation of a nitrile group. This step involves a nucleophilic substitution reaction where the diazonium group is replaced by the cyano group.

Step 4: Throughout the reaction, the alcohol group remains unchanged. The mechanism ensures that the alcohol oxygen in the reactant is the same in the product, maintaining the integrity of the ⍺-hydroxy acid structure.

Step 5: Finally, verify the transformation by comparing the structures. The amino group has been successfully replaced by a cyano group, and the alcohol group remains intact, resulting in the desired ⍺-hydroxy acid.

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Key Concepts

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

Amino Acid Structure and Reactivity

Amino acids are organic compounds that serve as the building blocks of proteins. They contain an amino group, a carboxyl group, and a side chain (R group) that determines their properties. Understanding the structure of amino acids is crucial for predicting their reactivity in chemical transformations, particularly in the synthesis of -hydroxy acids.

Mechanism of Organic Reactions

The mechanism of an organic reaction describes the step-by-step process by which reactants are converted into products. This includes the breaking and forming of bonds, the movement of electrons, and the intermediates formed during the reaction. A clear understanding of reaction mechanisms is essential for proposing a plausible pathway for the transformation of amino acids into -hydroxy acids.

Functional Group Interconversion

Functional group interconversion involves the transformation of one functional group into another within a molecule. In the context of synthesizing -hydroxy acids from amino acids, recognizing how to convert amino groups and carboxyl groups into hydroxyl groups is vital. This concept is key to understanding how the final product retains the same alcohol oxygen as the starting material.

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