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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5:30 minutes

Problem 72c

Textbook Question

How could you convert N-methylbenzamide to the following compounds?
c. methyl benzoate

Verified step by step guidance

Step 1: Recognize that N-methylbenzamide is an amide, and methyl benzoate is an ester. The conversion involves replacing the amide group (-CONHCH3) with an ester group (-COOCH3). This typically requires hydrolysis followed by esterification.

Step 2: Perform acidic or basic hydrolysis of N-methylbenzamide to break the amide bond. This will yield benzoic acid (C6H5COOH) and methylamine (CH3NH2). Use a strong acid like HCl or a strong base like NaOH for this step.

Step 3: Isolate the benzoic acid from the reaction mixture. If basic hydrolysis was used, acidify the solution to precipitate benzoic acid.

Step 4: React the benzoic acid with methanol (CH3OH) in the presence of an acid catalyst, such as sulfuric acid (H2SO4), to perform esterification. This will convert benzoic acid into methyl benzoate.

Step 5: Purify the methyl benzoate product using techniques such as distillation or recrystallization, depending on the reaction conditions and impurities.

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Key Concepts

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

Amide Hydrolysis

Amide hydrolysis is a reaction where an amide is converted into a carboxylic acid and an amine or ammonia, typically in the presence of water and an acid or base. This reaction is crucial for understanding how to transform N-methylbenzamide into its corresponding carboxylic acid, which can then be further converted into methyl benzoate.

Esterification

Esterification is the process of forming an ester from a carboxylic acid and an alcohol, usually in the presence of an acid catalyst. In this case, the carboxylic acid derived from the hydrolysis of N-methylbenzamide can react with methanol to produce methyl benzoate, illustrating the importance of this reaction in organic synthesis.

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 conversion of the carboxylic acid formed from N-methylbenzamide into the ester methyl benzoate, as the alcohol acts as the nucleophile.

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