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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4:02 minutes

Problem 18c

Textbook Question

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

Verified step by step guidance

Step 1: Identify the target compound, N,N-dimethylformamide (DMF). It is an amide with a formyl group (H-C=O) attached to a nitrogen atom that is substituted with two methyl groups.

Step 2: Recognize the starting materials needed for synthesis. To form an amide, you need a carboxylic acid and an amine. In this case, the carboxylic acid should be formic acid (HCOOH), and the amine should be dimethylamine ((CH₃)₂NH).

Step 3: Understand the reaction mechanism. The carboxylic acid reacts with the amine in the presence of a dehydrating agent (such as DCC or heat) to form the amide bond. This involves the removal of water (H₂O) during the reaction.

Step 4: Write the chemical equation for the synthesis: HCOOH + (CH₃)₂NH → HCON(CH₃)₂ + H₂O. This shows the formation of DMF and water as a byproduct.

Step 5: Ensure proper reaction conditions. Use a dehydrating agent or heat to drive the reaction forward and facilitate the formation of the amide bond. Monitor the reaction to ensure completion and purity of the product.

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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 a carboxyl group (-COOH). They are important in organic synthesis as they can react with amines to form amides. Understanding the reactivity and properties of carboxylic acids is crucial for synthesizing compounds like N,N-dimethylformamide (DMF), which involves the conversion of a carboxylic acid into an amide.

Amines

Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They play a significant role in organic synthesis, particularly in the formation of amides from carboxylic acids. In the case of DMF, dimethylamine is the amine used, highlighting the importance of understanding the structure and reactivity of different amines in synthesis.

Amide Formation

Amide formation is a key reaction in organic chemistry where a carboxylic acid reacts with an amine to produce an amide and water. This reaction is typically facilitated by heat or the presence of a coupling agent. For synthesizing DMF, the reaction between formic acid and dimethylamine exemplifies this process, showcasing the transformation of functional groups and the importance of understanding reaction mechanisms.

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Textbook Question

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

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

Textbook Question

Show how you would convert the following starting materials to the indicated nitriles:

(a) phenylacetic acid → phenylacetonitrile

Textbook Question

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

(a)

Textbook Question

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

(b)

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 appropriate acyl chlorides and amines to synthesize the following amides.

(a) N,N-dimethylacetamide

(b) acetanilide (PhNHCOCH₃)

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

Key Concepts

Carboxylic Acids

Amines

Amide Formation

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