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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4:34 minutes

Problem 16b

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the target compound. The given compound is an α,β-unsaturated ketone derived from cyclohexanone. This structure suggests the presence of a conjugated double bond adjacent to the carbonyl group.

Step 2: Identify the reaction type. To prepare an α,β-unsaturated ketone from cyclohexanone, an aldol condensation reaction is typically used. This involves the formation of a β-hydroxy ketone intermediate followed by dehydration to form the conjugated double bond.

Step 3: Choose the appropriate reagent. To achieve the desired transformation, cyclohexanone can be reacted with acetaldehyde (CH₃CHO) in the presence of a base such as NaOH or KOH. The base facilitates the enolate formation from cyclohexanone, which then reacts with acetaldehyde.

Step 4: Describe the mechanism. The reaction proceeds as follows: (a) Cyclohexanone forms an enolate ion under basic conditions. (b) The enolate ion attacks the carbonyl carbon of acetaldehyde, forming a β-hydroxy ketone intermediate. (c) Under heating or continued basic conditions, the β-hydroxy ketone undergoes dehydration to yield the α,β-unsaturated ketone.

Step 5: Verify the product. The final product matches the target compound, with the conjugated double bond adjacent to the cyclohexanone ring. This confirms the successful application of the aldol condensation reaction.

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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, this can lead to the formation of alcohols or other functional groups depending on the nucleophile used. Mastery of this concept is essential for synthesizing desired products from cyclohexanone.

Functional Group Transformations

Functional group transformations are chemical reactions that convert one functional group into another, allowing for the modification of organic compounds. In the context of cyclohexanone, understanding how to perform these transformations, such as reduction or oxidation, is key to preparing various derivatives from the starting material.

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