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

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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2:57 minutes

Problem 85a

Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
a.

Verified step by step guidance

Step 1: Identify the functional group transformation. The starting material is an amide (CH3CH2(C=O)NH2), and the target compound is an acyl chloride (CH3CH2(C=O)Cl). This transformation involves replacing the -NH2 group with a -Cl group.

Step 2: Recognize the reagent required for this transformation. Amides can be converted to acyl chlorides using reagents such as thionyl chloride (SOCl2) or phosphorus pentachloride (PCl5). These reagents facilitate the substitution of the amide group with a chlorine atom.

Step 3: Write the reaction mechanism. When thionyl chloride (SOCl2) is used, the amide reacts with SOCl2 to form an intermediate, which then eliminates sulfur dioxide (SO2) and hydrogen chloride (HCl) to yield the acyl chloride.

Step 4: Ensure proper reaction conditions. The reaction typically occurs under mild heating to ensure the complete conversion of the amide to the acyl chloride.

Step 5: Verify the product structure. After the reaction, the product should have the desired acyl chloride functional group (CH3CH2(C=O)Cl), replacing the original amide group.

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Key Concepts

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

Amides and Their Reactivity

Amides are organic compounds characterized by a carbonyl group (C=O) attached to a nitrogen atom (N). They can undergo various reactions, including hydrolysis and conversion to acyl chlorides. Understanding the reactivity of amides is crucial for predicting their transformation into other functional groups, such as acyl chlorides, which are more reactive and useful in further synthetic applications.

Acyl Chloride Formation

Acyl chlorides are derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom (-Cl). This transformation can be achieved through the reaction of an amide with reagents like thionyl chloride (SOCl2) or oxalyl chloride (COCl)2. Recognizing the conditions and reagents necessary for this conversion is essential for successfully synthesizing acyl chlorides from amides.

Reagents in Organic Synthesis

In organic synthesis, various reagents are employed to facilitate chemical transformations. For the conversion of amides to acyl chlorides, reagents such as thionyl chloride or phosphorus pentachloride are commonly used. Understanding the role of these reagents, including their mechanisms and the conditions under which they operate, is vital for designing effective synthetic pathways in organic chemistry.

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Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.a.

Key Concepts

Amides and Their Reactivity

Acyl Chloride Formation

Reagents in Organic Synthesis

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Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
a.