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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3:49 minutes

Problem 42g

Textbook Question

Using any necessary reagents, show how you would accomplish the following syntheses.
(g)

Verified step by step guidance

Step 1: Analyze the starting material and product. The starting material is a carboxylic acid, and the product is an amide. This transformation involves converting the carboxylic acid functional group (-COOH) into an amide (-CONR2).

Step 2: To convert a carboxylic acid into an amide, first activate the carboxylic acid. This can be done by converting it into an acid chloride using reagents like thionyl chloride (SOCl2) or oxalyl chloride. The reaction replaces the hydroxyl group (-OH) with a chlorine atom (-Cl), forming an acid chloride.

Step 3: Once the acid chloride is formed, it can react with an amine to form the desired amide. In this case, the amine used is diethylamine (H-N(CH2CH3)2). The nucleophilic amine attacks the carbonyl carbon of the acid chloride, leading to the formation of the amide bond.

Step 4: During the reaction between the acid chloride and the amine, a byproduct such as HCl is formed. To neutralize this byproduct, a base like pyridine or triethylamine can be added to the reaction mixture.

Step 5: After the reaction is complete, purify the product using techniques like extraction or recrystallization to isolate the desired amide.

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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 reactions, including esterification and conversion to acid chlorides. Understanding their structure and reactivity is crucial for predicting the outcomes of synthetic transformations.

Acid Chlorides

Acid chlorides, also known as acyl chlorides, are derivatives of carboxylic acids where the hydroxyl group is replaced by a chlorine atom. They are highly reactive and serve as important intermediates in organic synthesis, particularly in the formation of amides and esters. Recognizing their formation from carboxylic acids is essential for understanding the reaction mechanisms involved.

Reagents for Conversion

The conversion of carboxylic acids to acid chlorides typically involves reagents such as thionyl chloride (SOCl2), oxalyl chloride (COCl)2, or phosphorus pentachloride (PCl5). These reagents facilitate the substitution of the hydroxyl group with a chlorine atom, enabling the transformation. Familiarity with these reagents and their mechanisms is vital for successful synthesis in organic chemistry.

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