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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3:30 minutes

Problem 68c

Textbook Question

What are the products of the following reactions?
c.

Verified step by step guidance

Step 1: Analyze the starting material. The given compound is a cyclopentane ring with a carboxylic acid group (-COOH) attached to it.

Step 2: Understand the role of SOCl2 (thionyl chloride). SOCl2 reacts with carboxylic acids to convert the -COOH group into an acyl chloride (-COCl). This reaction involves the replacement of the hydroxyl group (-OH) in the carboxylic acid with a chlorine atom.

Step 3: Examine the second reagent, CH3CH2NH2 (ethylamine). Acyl chlorides are highly reactive and can undergo nucleophilic substitution with amines. In this case, the ethylamine will attack the acyl chloride, replacing the chlorine atom and forming an amide bond (-CONH-).

Step 4: Combine the transformations. The first step converts the carboxylic acid into an acyl chloride, and the second step converts the acyl chloride into an amide. The final product will be a cyclopentane ring with an amide group (-CONHCH2CH3) attached.

Step 5: Verify the structure of the product. The product is N-ethylcyclopentanecarboxamide, where the amide group is directly attached to the cyclopentane ring.

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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 known for their acidic properties and can undergo various chemical reactions, including conversion to acid chlorides. Understanding their structure and reactivity is essential for predicting the products of reactions involving them.

Thionyl Chloride (SOCl2)

Thionyl chloride (SOCl2) is a reagent commonly used to convert carboxylic acids into acid chlorides. This reaction involves the substitution of the hydroxyl group (-OH) of the carboxylic acid with a chlorine atom, resulting in the formation of an acid chloride. This step is crucial in the reaction sequence provided in the question.

Amine Nucleophiles

Amines, such as methylamine (CH3NH2), act as nucleophiles in organic reactions. They can react with acid chlorides to form amides through nucleophilic acyl substitution. Understanding the role of amines in these reactions is vital for predicting the final products when they react with acid chlorides.

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