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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5:49 minutes

Problem 56a

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.
(a) octan-1-ol

Verified step by step guidance

Identify the functional group in the starting compound, octan-1-ol. It contains a primary alcohol (-OH) group attached to the first carbon of an eight-carbon chain.

Recall that to synthesize an aldehyde (octanal) from a primary alcohol, a mild oxidation reaction is required. Strong oxidizing agents would over-oxidize the alcohol to a carboxylic acid, so a selective oxidizing agent is necessary.

Choose an appropriate reagent for mild oxidation. Common reagents include PCC (Pyridinium Chlorochromate) or DMP (Dess-Martin Periodinane), which selectively oxidize primary alcohols to aldehydes without further oxidation to carboxylic acids.

Write the reaction mechanism: The primary alcohol undergoes oxidation, where the hydroxyl group (-OH) is converted into a carbonyl group (C=O) on the same carbon, resulting in the formation of octanal.

Ensure proper reaction conditions: Perform the reaction in an anhydrous solvent (e.g., dichloromethane) to prevent over-oxidation and maintain the aldehyde as the final product.

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Key Concepts

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

Oxidation of Alcohols

The conversion of alcohols to aldehydes or ketones involves oxidation reactions. In the case of primary alcohols like octan-1-ol, oxidation can be achieved using reagents such as potassium dichromate or PCC (pyridinium chlorochromate). This process transforms the hydroxyl (-OH) group into a carbonyl (C=O) group, yielding octanal as the product.

Reagents for Organic Synthesis

Understanding the appropriate reagents for organic synthesis is crucial. For synthesizing octanal from octan-1-ol, oxidizing agents like CrO3 or Na2Cr2O7 can be used. Additionally, knowledge of reaction conditions, such as temperature and solvent, is essential to ensure the desired transformation occurs efficiently and selectively.

Functional Group Transformation

Functional group transformation is a key concept in organic chemistry, where one functional group is converted into another. In this case, the transformation of the alcohol functional group (-OH) in octan-1-ol to the aldehyde functional group (C=O) in octanal is a classic example. This concept is fundamental for understanding how to manipulate organic compounds to achieve desired products.

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