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 Derivatives

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

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2:41 minutes

Problem 48a

Textbook Question

Show how you would accomplish the following syntheses in good yields.
(a)

Verified step by step guidance

Step 1: Identify the starting material and the target product. The starting material is aniline (C₆H₅NH₂), and the target product is benzamide (C₆H₅CONH₂). This transformation involves converting the amino group (-NH₂) into an amide group (-CONH₂).

Step 2: Recognize the reagent required for this transformation. To convert an amine into an amide, an acylating agent such as acetic anhydride (CH₃CO)₂O or an acyl chloride (e.g., CH₃COCl) can be used. In this case, formyl chloride (HCOCl) is appropriate to introduce the formyl group (-CHO).

Step 3: Write the reaction mechanism. The nucleophilic amino group (-NH₂) of aniline attacks the electrophilic carbon of the formyl chloride (HCOCl), leading to the formation of an intermediate. This intermediate undergoes deprotonation to yield benzamide.

Step 4: Consider reaction conditions. The reaction typically requires a base such as pyridine or triethylamine to neutralize the HCl byproduct and facilitate the reaction. The reaction is carried out under mild conditions to avoid overreaction or degradation of the product.

Step 5: Purify the product. After the reaction is complete, the crude product can be purified using techniques such as recrystallization or column chromatography to obtain benzamide in good yield.

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Key Concepts

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

Amine Reactivity

Amines are organic compounds derived from ammonia, characterized by the presence of one or more alkyl or aryl groups attached to a nitrogen atom. They can act as nucleophiles in chemical reactions, meaning they can donate a pair of electrons to form bonds with electrophiles. Understanding the reactivity of amines is crucial for predicting their behavior in synthesis, particularly in forming derivatives like amides.

Carboxylic Acid Derivatives

Carboxylic acid derivatives include compounds such as esters, amides, and anhydrides, which are derived from carboxylic acids. They retain the carboxyl functional group but have different substituents that influence their reactivity and properties. In the context of the synthesis shown, converting an amine to an amide (a type of carboxylic acid derivative) is a common transformation in organic chemistry.

Synthesis Strategies

Synthesis strategies in organic chemistry involve planning and executing a series of chemical reactions to construct a desired compound. This includes selecting appropriate reagents, conditions, and reaction pathways to achieve high yields. In the given synthesis, understanding how to effectively convert an amine to an amide through specific reagents and conditions is essential for successful execution.

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Show how you would accomplish the following syntheses in good yields.(a)

Key Concepts

Amine Reactivity

Carboxylic Acid Derivatives

Synthesis Strategies

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Show how you would accomplish the following syntheses in good yields.
(a)