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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7:40 minutes

Problem 47b

Textbook Question

How could you synthesize the following compounds starting with a carboxylic acid?
b.

Verified step by step guidance

Step 1: Begin with a carboxylic acid that has the aromatic ring structure with a nitro group (-NO2) in the para position. This will serve as the starting material for the synthesis.

Step 2: Convert the carboxylic acid group (-COOH) into an acid chloride (-COCl) using a reagent such as thionyl chloride (SOCl2). This step activates the carboxylic acid for further reactions.

Step 3: Perform an amide formation reaction by reacting the acid chloride with cyclopentylamine (C5H9NH2). This will result in the formation of the desired amide bond (-CONH-). Use a base like pyridine to neutralize the HCl byproduct.

Step 4: Ensure the reaction conditions are mild to avoid any side reactions, such as reduction of the nitro group (-NO2) or overreaction of the amine.

Step 5: Purify the final product using techniques such as recrystallization or column chromatography to isolate the desired compound with the nitro group intact and the amide bond formed.

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Key Concepts

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

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are important in organic synthesis as they can be converted into various derivatives, such as acid chlorides, esters, and amides. Understanding their reactivity and functional group transformations is crucial for synthesizing more complex molecules.

Acid Chlorides

Acid chlorides, also known as acyl chlorides, are derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom. They are highly reactive intermediates in organic synthesis, often used to form esters and amides. Their ability to react with nucleophiles makes them valuable in constructing various organic compounds.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. This mechanism is key in the transformation of acid chlorides into other functional groups, such as amides or esters, and is essential for understanding the synthesis of complex organic molecules.

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