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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Malonic Ester Synthesis

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Malonic Ester Synthesis

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8:03 minutes

Problem 21Bruice - 8th Edition

Textbook Question

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step? a. (CH3)2CHCH2Br

Verified step by step guidance

Identify the starting material for the N-phthalimidomalonic ester synthesis, which is the N-phthalimidomalonic ester itself.

In the third step of the synthesis, the alkyl halide (in this case, (CH3)2CHCH2Br) is used to alkylate the malonic ester derivative. This involves a nucleophilic substitution reaction where the carbanion generated from the malonic ester attacks the alkyl halide.

Determine the structure of the alkyl group that will be attached to the malonic ester. Here, the alkyl group is (CH3)2CHCH2-, which is an isobutyl group.

After the alkylation step, the compound undergoes hydrolysis and decarboxylation. The hydrolysis converts the ester groups into carboxylic acids, and decarboxylation removes one of the carboxyl groups, forming an amino acid.

The final amino acid structure will have the isobutyl group as the side chain, which corresponds to the amino acid leucine.

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Key Concepts

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

N-phthalimidomalonic ester synthesis

N-phthalimidomalonic ester synthesis is a method for synthesizing amino acids, where a phthalimide is reacted with malonic ester to form an intermediate. This intermediate can then undergo alkylation, typically involving an alkyl halide, to introduce a side chain. The process ultimately leads to the formation of an amino acid after hydrolysis and decarboxylation.

Alkylation

Alkylation is a chemical reaction that involves the transfer of an alkyl group from one molecule to another. In the context of the N-phthalimidomalonic ester synthesis, the alkyl halide (in this case, (CH3)2CHCH2Br) is used to introduce a branched alkyl chain into the malonic ester intermediate. This step is crucial for determining the structure of the resulting amino acid.

Amino acid structure

Amino acids are organic compounds that serve as the building blocks of proteins. Each amino acid has a central carbon atom bonded to an amino group, a carboxyl group, a hydrogen atom, and a variable side chain (R group). The specific side chain introduced during the synthesis determines the identity and properties of the resulting amino acid, influencing its role in biological systems.