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

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid to Acid Chloride

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid to Acid Chloride

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3:56 minutes

Problem 36d

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(d) hexanoic acid → hexanal

Verified step by step guidance

Step 1: Recognize that the transformation involves converting a carboxylic acid (hexanoic acid) into an aldehyde (hexanal). This requires reducing the carboxylic acid selectively to the aldehyde without over-reduction to the alcohol.

Step 2: Use a reagent that can selectively reduce carboxylic acids to aldehydes. One common choice is the use of a mild reducing agent such as DIBAL-H (Diisobutylaluminum hydride). DIBAL-H is known for its ability to stop at the aldehyde stage during reduction.

Step 3: Set up the reaction conditions. Add DIBAL-H to hexanoic acid at low temperatures (e.g., -78°C) to ensure controlled reduction. This prevents over-reduction to the alcohol.

Step 4: After the reaction is complete, quench the reaction by adding water or a mild acid to hydrolyze the intermediate and isolate the aldehyde product.

Step 5: Purify the hexanal product using techniques such as distillation or chromatography to ensure the desired compound is obtained in high purity.

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Key Concepts

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

Oxidation-Reduction Reactions

Oxidation-reduction (redox) reactions are fundamental in organic chemistry, involving the transfer of electrons between substances. In the synthesis of hexanal from hexanoic acid, a reduction reaction is necessary, where the carboxylic acid group (-COOH) of hexanoic acid is converted to an aldehyde group (-CHO) in hexanal. Understanding the principles of oxidation states and the role of reducing agents is crucial for this transformation.

Reagents for Reduction

Selecting appropriate reagents is essential for effective organic synthesis. Common reducing agents for converting carboxylic acids to aldehydes include lithium aluminum hydride (LiAlH4) or borane (BH3). These reagents facilitate the reduction process by donating electrons, thus enabling the conversion of the carboxylic acid functional group to an aldehyde while minimizing over-reduction to alcohols.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another, which is a key concept in organic synthesis. In this case, converting hexanoic acid (a carboxylic acid) to hexanal (an aldehyde) exemplifies this process. Mastery of functional group interconversions allows chemists to design synthetic pathways and manipulate molecular structures effectively.

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