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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Acetoacetic Ester Synthesis

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Acetoacetic Ester Synthesis

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2:16 minutes

Problem 66c

Textbook Question

Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:
c.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is an ethyl acetoacetate derivative, and the target compound is a ketone with a cyclohexyl group attached. This suggests that a nucleophilic substitution followed by cyclization is required.

Step 2: Perform an alkylation reaction on the ethyl acetoacetate derivative. Use a suitable alkyl halide, such as bromocyclohexane, and a strong base like sodium ethoxide (NaOEt) to deprotonate the alpha-carbon of the starting material. This generates a nucleophilic enolate ion that can attack the alkyl halide, forming a new C-C bond.

Step 3: Hydrolyze the ester group in the alkylated product. Use acidic or basic hydrolysis conditions to convert the ester group into a carboxylic acid. This step prepares the molecule for decarboxylation.

Step 4: Decarboxylate the carboxylic acid under heating conditions. This step removes the carboxyl group, leaving behind the desired ketone structure with the cyclohexyl group attached.

Step 5: Purify the final product using appropriate techniques such as distillation or recrystallization to isolate the target ketone compound.

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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 compound can then undergo hydrolysis and decarboxylation to yield a ketone.

Enolate Chemistry

Enolates are reactive intermediates formed from the deprotonation of carbonyl compounds, such as esters or ketones. They are crucial in nucleophilic addition reactions, where they can act as nucleophiles to attack electrophiles. Understanding enolate stability and reactivity is essential for predicting the outcomes of reactions involving acetoacetic esters and other carbonyl compounds.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions significantly influences the outcome of organic reactions. In acetoacetic ester synthesis, common reagents include strong bases (like sodium ethoxide) for deprotonation and alkyl halides for alkylation. Additionally, controlling temperature and solvent can affect the reaction rate and selectivity, making it vital to understand these factors for successful synthesis.

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Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:c.

Key Concepts

Acetoacetic Ester Synthesis

Enolate Chemistry

Reagents and Reaction Conditions

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Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:
c.