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

Previous problemNext problem

3:21 minutes

Problem 9a,b

Textbook Question

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH₃)

Verified step by step guidance

Identify the general reaction for amide synthesis: Amides can be synthesized by reacting an acyl chloride with an amine. The reaction involves nucleophilic acyl substitution, where the amine attacks the carbonyl carbon of the acyl chloride, leading to the formation of the amide and the release of HCl.

For part (a), N,N-dimethylacetamide: Determine the required acyl chloride and amine. The structure of N,N-dimethylacetamide suggests that the acyl chloride should be acetyl chloride (CH3COCl), and the amine should be dimethylamine ((CH3)2NH).

Write the reaction for part (a): Combine acetyl chloride (CH3COCl) with dimethylamine ((CH3)2NH). The reaction proceeds as follows:

CH 3_{COCl} + {(CH}_{3})_{2} NH → {CH}_{3} {CON(CH}_{3})_{2} + HCl

For part (b), acetanilide (PhNHCOCH3): Determine the required acyl chloride and amine. The structure of acetanilide suggests that the acyl chloride should again be acetyl chloride (CH3COCl), and the amine should be aniline (PhNH2).

Write the reaction for part (b): Combine acetyl chloride (CH3COCl) with aniline (PhNH2). The reaction proceeds as follows:

CH 3_{COCl} + PhNH 2 → PhNHCOCH 3 + HCl

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Acyl Chlorides

Acyl chlorides, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom. They are highly reactive towards nucleophiles, making them useful in organic synthesis, particularly for forming amides. In the context of the question, acyl chlorides can be reacted with amines to produce the desired amides.

Amines

Amines are organic compounds that contain nitrogen atoms bonded to carbon atoms. They can act as nucleophiles due to the lone pair of electrons on the nitrogen, allowing them to react with electrophiles like acyl chlorides. In synthesizing amides, the amine reacts with the acyl chloride to form the amide bond, releasing hydrochloric acid as a byproduct.

Amide Formation

Amide formation is a key reaction in organic chemistry where an amine reacts with a carboxylic acid derivative, such as an acyl chloride, to produce an amide. This reaction typically involves nucleophilic attack by the amine on the carbonyl carbon of the acyl chloride, leading to the formation of the amide bond (C=O-N). Understanding this mechanism is crucial for synthesizing specific amides like N,N-dimethylacetamide and acetanilide.

Watch next

Master NAS - The Three Rules with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(c)

Textbook Question

Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

Textbook Question

Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an S_N2 reaction?

Textbook Question

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

(e) tert-butyl acetate

(f) diallyl succinate

Textbook Question

Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol

Textbook Question

Predict the products of the following reactions.

(a)

Textbook Question

Predict the products of the following reactions.

(b)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.(a) N,N-dimethylacetamide(b) acetanilide (PhNHCOCH3)

Key Concepts

Acyl Chlorides

Amines

Amide Formation

Watch next

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH₃)