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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4:03 minutes

Problem 65h

Textbook Question

Identify A through O:

Verified step by step guidance

Step 1: Analyze the starting compound. The molecule contains two ketone groups and one carboxylic acid group. The carboxylic acid group is reactive and can undergo substitution reactions.

Step 2: Understand the role of SOCl₂. SOCl₂ (thionyl chloride) is commonly used to convert carboxylic acids into acyl chlorides. The reaction replaces the hydroxyl group (-OH) of the carboxylic acid with a chlorine atom (-Cl), forming an acyl chloride.

Step 3: Predict the structure of compound A. After the reaction with SOCl₂, the carboxylic acid group in the starting compound is converted into an acyl chloride. The ketone groups remain unchanged.

Step 4: Examine the second reaction. Compound A reacts with CH₃OH (methanol). Methanol can act as a nucleophile, attacking the carbonyl carbon of the acyl chloride group. This results in the formation of an ester, where the chlorine atom is replaced by the methoxy group (-OCH₃).

Step 5: Predict the structure of compound B. After the reaction with methanol, the acyl chloride group in compound A is converted into a methyl ester. The ketone groups remain unchanged throughout the process.

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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 one or more carboxyl groups (-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 outcomes of reactions involving these functional groups.

Thionyl Chloride (SOCl2) Reaction

Thionyl chloride (SOCl2) is commonly used to convert carboxylic acids into acid chlorides. This reaction involves the nucleophilic attack of the carboxylic acid on SOCl2, leading to the formation of the acid chloride and the byproducts of sulfur dioxide (SO2) and hydrochloric acid (HCl). This transformation is significant in organic synthesis for creating more reactive intermediates.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of the reaction shown, methanol (CH3OH) acts as a nucleophile that can attack the acid chloride formed in the previous step, resulting in the formation of an ester. Understanding this mechanism is crucial for predicting product formation in organic reactions.