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

25. Condensation Chemistry

Michael Addition

Organic Chemistry

25. Condensation Chemistry

Michael Addition

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9:21 minutes

Problem 54

Textbook Question

Show how an acetoacetic ester synthesis might be used to form a δ-diketone such as heptane-2,6-dione.

Verified step by step guidance

Identify the starting material for the acetoacetic ester synthesis. The key reagent is ethyl acetoacetate (CH₃COCH₂COOEt), which contains both a ketone and an ester functional group, making it a versatile compound for this reaction.

Determine the alkyl halides needed to form the δ-diketone. In this case, the target molecule, heptane-2,6-dione, suggests that two alkyl groups (ethyl groups) need to be added to the central carbon of ethyl acetoacetate.

Perform the first alkylation. Deprotonate the methylene group (CH₂) of ethyl acetoacetate using a strong base such as sodium ethoxide (NaOEt) to form an enolate ion. Then, react the enolate with ethyl bromide (C₂H₅Br) to add the first ethyl group.

Perform the second alkylation. Repeat the process by deprotonating the remaining methylene hydrogen of the monoalkylated product with a strong base, forming a new enolate ion. React this enolate with another equivalent of ethyl bromide to add the second ethyl group.

Hydrolyze and decarboxylate the diethylated product. Treat the compound with aqueous acid (H₃O⁺) to hydrolyze the ester group to a carboxylic acid. Then, heat the resulting β-keto acid to induce decarboxylation, yielding the desired δ-diketone, heptane-2,6-dione.

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Key Concepts

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

Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method for forming ketones through the reaction of an acetoacetic ester with an alkyl halide. This process involves the enolate ion of the acetoacetic ester attacking the alkyl halide, leading to the formation of a new carbon-carbon bond. The resulting product can be hydrolyzed and decarboxylated to yield a diketone, making it a valuable reaction in organic synthesis.

Diketones

Diketones are organic compounds that contain two carbonyl groups (C=O) within the same molecule. They can exhibit unique chemical properties and reactivity due to the presence of these functional groups. In the case of heptane-2,6-dione, the diketone structure allows for various synthetic applications, including the formation of complex molecules and intermediates in organic chemistry.

Enolate Chemistry

Enolate chemistry involves the formation and reactivity of enolate ions, which are generated from carbonyl compounds through deprotonation. These enolate ions are nucleophilic and can participate in various reactions, such as alkylation and condensation. Understanding enolate chemistry is crucial for acetoacetic ester synthesis, as it enables the formation of new carbon-carbon bonds necessary for constructing diketones like heptane-2,6-dione.

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