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

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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3:19 minutes

Problem 6d

Textbook Question

Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

Verified step by step guidance

Step 1: Identify the reactants and the product. The reactants are aniline (C6H5NH2) and acetic anhydride ((CH3CO)2O), and the product is acetanilide (C6H5NHCOCH3). This reaction involves the acetylation of aniline.

Step 2: Recognize the nucleophilic site on aniline. The nitrogen atom in aniline has a lone pair of electrons, making it nucleophilic and capable of attacking the electrophilic carbonyl carbon in acetic anhydride.

Step 3: Initiate the reaction mechanism. The lone pair of electrons on the nitrogen atom of aniline attacks one of the carbonyl carbons in acetic anhydride, forming a tetrahedral intermediate. This step involves nucleophilic addition.

Step 4: Eliminate the leaving group. The tetrahedral intermediate collapses, expelling the acetate ion (CH3COO−) as a leaving group. This step results in the formation of the amide bond between the nitrogen of aniline and the acetyl group.

Step 5: Finalize the product. The reaction yields acetanilide (C6H5NHCOCH3) as the final product, with acetate ion as a byproduct. This is an example of an acylation reaction where aniline is converted into an amide.

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Key Concepts

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

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbonyl carbon, leading to the substitution of a leaving group. In the case of aniline reacting with acetic anhydride, the amino group of aniline acts as the nucleophile, attacking the carbonyl carbon of the acetic anhydride, resulting in the formation of acetanilide.

Role of Acetic Anhydride

Acetic anhydride is a reactive acylating agent commonly used in organic synthesis. It provides an acyl group (CH3CO-) that can be transferred to nucleophiles. In this reaction, acetic anhydride not only serves as the source of the acyl group but also facilitates the formation of the amide bond in acetanilide by releasing acetic acid as a byproduct.

Amide Formation

Amide formation is a key reaction in organic chemistry where a carboxylic acid or its derivative reacts with an amine to form an amide. In this case, the reaction between aniline and acetic anhydride results in the formation of acetanilide, an amide, through the nucleophilic attack of the aniline nitrogen on the carbonyl carbon of the acetic anhydride, followed by the elimination of acetic acid.

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Related Practice

Textbook Question

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.

(a) ethanol

(b) sodium acetate

Textbook Question

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(d)

Textbook Question

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(a) ethyl propionate

(b) phenyl 3-methylhexanoate

Textbook Question

Which of the following proposed reactions would take place quickly under mild conditions?

(a)

(b)

(c)

(d)

(e)

Textbook Question

Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

Textbook Question

Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(g)

Textbook Question

Show how you would use an acid chloride as an intermediate to synthesize.

(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline.

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