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

Enolate Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

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4:58 minutes

Problem 16a

Textbook Question

How could each of the following compounds be prepared from cyclohexanone?
a.

Verified step by step guidance

Step 1: Analyze the target compound. The target compound is a ketone with a butyl group attached to the alpha-carbon of cyclohexanone. This suggests an alkylation reaction at the alpha-carbon of cyclohexanone.

Step 2: Identify the reagent needed for alkylation. To introduce a butyl group, you would use a butyl halide (e.g., 1-bromobutane or 1-chlorobutane) as the alkylating agent.

Step 3: Prepare cyclohexanone for alkylation. Cyclohexanone must first be converted into its enolate form. This can be achieved by treating cyclohexanone with a strong base such as sodium hydride (NaH) or lithium diisopropylamide (LDA). The base deprotonates the alpha-carbon, forming the enolate ion.

Step 4: Perform the alkylation reaction. The enolate ion reacts with the butyl halide in an SN2 mechanism, where the halide is displaced, and the butyl group is attached to the alpha-carbon of cyclohexanone.

Step 5: Purify the product. After the reaction is complete, the mixture can be purified using techniques such as distillation or chromatography to isolate the desired compound.

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Key Concepts

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

Cyclohexanone Structure and Reactivity

Cyclohexanone is a cyclic ketone with a six-membered carbon ring and a carbonyl group (C=O). Its structure makes it a versatile intermediate in organic synthesis, allowing for various reactions such as nucleophilic addition and oxidation. Understanding its reactivity is crucial for determining how to convert it into other compounds.

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile on the electrophilic carbon of a carbonyl group. In the case of cyclohexanone, nucleophiles can add to the carbonyl carbon, leading to the formation of alcohols or other functional groups. This concept is essential for synthesizing derivatives from cyclohexanone.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another. In organic synthesis, these transformations are key to modifying compounds like cyclohexanone into desired products. Familiarity with common reactions, such as reduction, oxidation, and substitution, is necessary for planning the synthesis of target compounds.

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