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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1:51 minutes

Problem 69c,d

Textbook Question

Phosgene (COCl₂) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents?
c. excess propylamine
d. excess water

Verified step by step guidance

Step 1: Understand the structure and reactivity of phosgene (COCl₂). Phosgene is a reactive compound with a carbonyl group (C=O) bonded to two chlorine atoms. It is an electrophile and reacts readily with nucleophiles such as amines and water.

Step 2: Analyze the reaction with excess propylamine (C₃H₇NH₂). Propylamine is a nucleophile due to the lone pair on the nitrogen atom. In the presence of excess propylamine, phosgene undergoes nucleophilic substitution reactions where the chlorine atoms are replaced by propylamine groups.

Step 3: Write the mechanism for the reaction with propylamine. The first step involves the attack of the nitrogen's lone pair on the carbonyl carbon of phosgene, displacing one chlorine atom. This process repeats with the second chlorine atom, resulting in the formation of a bis(propylamino)carbonyl compound: CO(NHC₃H₇)₂.

Step 4: Analyze the reaction with excess water. Water is also a nucleophile due to the lone pairs on oxygen. In the presence of excess water, phosgene undergoes hydrolysis, where the chlorine atoms are replaced by hydroxyl groups, forming carbonic acid (H₂CO₃).

Step 5: Write the mechanism for the reaction with water. The first step involves the attack of water's oxygen on the carbonyl carbon of phosgene, displacing one chlorine atom. This process repeats with the second chlorine atom, resulting in the formation of carbonic acid (H₂CO₃). Carbonic acid may further decompose into CO₂ and H₂O under certain conditions.

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Key Concepts

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

Reactivity of Phosgene

Phosgene (COCl2) is a reactive carbonyl compound that can undergo nucleophilic addition reactions. The carbon atom in phosgene is electrophilic due to the presence of the electron-withdrawing chlorine atoms, making it susceptible to attack by nucleophiles such as amines and water. Understanding this reactivity is crucial for predicting the products formed when phosgene reacts with different reagents.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. In the case of phosgene reacting with propylamine, the amine acts as a nucleophile, attacking the carbonyl carbon and displacing a chlorine atom. This concept is essential for determining the structure of the product formed when phosgene reacts with amines.

Hydrolysis of Carbonyl Compounds

Hydrolysis is the reaction of a compound with water, leading to the breakdown of that compound. When phosgene reacts with excess water, it undergoes hydrolysis to form carbonic acid and hydrochloric acid. This process is important for understanding how phosgene can be neutralized in the presence of water and the resulting products of such a reaction.

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Show how you would accomplish the following syntheses using amides as intermediates. You may use any necessary reagents.

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(b) pyrrolidine → N-ethylpyrrolidine

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Predict the major, organic product for the following reaction.

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Predict the major, organic product for the following reaction.

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When a student treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.

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Propose a mechanism for the reaction of benzoic acid with oxalyl chloride. This mechanism begins like the thionyl chloride reaction, to give a reactive mixed anhydride. Nucleophilic acyl substitution by chloride ion gives a tetrahedral intermediate that eliminates a leaving group, which then fragments into carbon dioxide, carbon monoxide, and chloride ion.

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What reagents are required to carry out the following synthesis?

Textbook Question

Predict the product of the following reactions.

(a)

Textbook Question

Predict the product of the following reactions.

(c)

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