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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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5:47 minutes

Problem 12

Textbook Question

Show how the following compounds can be synthesized from cyclohexanol.
a. b. c.

Verified step by step guidance

Step 1: Begin by analyzing the target compounds (a, b, c) and identify the functional groups or structural changes that differentiate them from cyclohexanol. For example, determine if oxidation, substitution, or elimination reactions are required.

Step 2: For each target compound, determine the appropriate reaction pathway starting from cyclohexanol. For instance, if the target compound involves a ketone, consider oxidizing cyclohexanol to cyclohexanone using an oxidizing agent like PCC (Pyridinium chlorochromate).

Step 3: If the target compound involves a double bond (alkene), consider performing an elimination reaction. Dehydrate cyclohexanol using a strong acid like H2SO4 to form cyclohexene via an E1 mechanism.

Step 4: If the target compound involves further functional group transformations (e.g., halogenation, epoxidation, or hydroxylation), identify the reagents and conditions required for each step. For example, cyclohexene can be brominated using Br2 to form a dibromo compound or epoxidized using mCPBA (meta-chloroperoxybenzoic acid).

Step 5: Combine all the steps into a coherent synthetic pathway for each target compound, ensuring that the reagents and conditions are compatible and that the intermediate products are stable under the reaction conditions.

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Key Concepts

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

Alcohol Dehydration

Alcohol dehydration is a chemical reaction where an alcohol loses a water molecule, typically resulting in the formation of an alkene. This process often requires an acid catalyst and can occur through either an E1 or E2 mechanism, depending on the structure of the alcohol and the reaction conditions. Understanding this concept is crucial for synthesizing compounds from cyclohexanol, as it allows for the conversion of the alcohol into more reactive intermediates.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of synthesizing compounds from cyclohexanol, this concept is essential for understanding how to convert alcohols into other functional groups, such as halides or ethers, through reactions like SN1 or SN2 mechanisms. The choice of nucleophile and reaction conditions significantly influences the outcome of the synthesis.

Oxidation of Alcohols

The oxidation of alcohols is a fundamental reaction in organic chemistry where alcohols are converted into carbonyl compounds, such as aldehydes or ketones, or further to carboxylic acids. This transformation is typically achieved using oxidizing agents like potassium dichromate or PCC. Recognizing how to oxidize cyclohexanol is vital for synthesizing various target compounds, as it alters the functional groups present in the molecule.

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