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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6:07 minutes

Problem 75a

Textbook Question

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

Verified step by step guidance

Step 1: Begin with the starting material, toluene (C6H5CH3). The methyl group on the benzene ring will serve as the site for functionalization.

Step 2: Perform a benzylic oxidation of the methyl group using a strong oxidizing agent such as KMnO4 or Na2Cr2O7 under acidic conditions. This will convert the methyl group (-CH3) into a carboxylic acid group (-COOH), yielding benzoic acid (C6H5COOH).

Step 3: Convert the benzoic acid into an acid chloride (-COCl) by treating it with thionyl chloride (SOCl2). This reaction replaces the hydroxyl group (-OH) of the carboxylic acid with a chlorine atom, forming benzoyl chloride (C6H5COCl).

Step 4: React the benzoyl chloride with ethylamine (CH3CH2NH2) in the presence of a base such as pyridine. This nucleophilic acyl substitution will replace the chlorine atom with the ethylamine group, forming the desired amide product, N-ethylbenzamide (C6H5CONHCH2CH3).

Step 5: Purify the final product using standard organic purification techniques such as recrystallization or chromatography to ensure the desired compound is obtained in high purity.

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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 in organic chemistry where a nucleophile attacks an acyl compound, leading to the replacement of a leaving group with the nucleophile. In this process, the carbonyl carbon becomes electrophilic, allowing the nucleophile to form a tetrahedral intermediate, which then collapses to release the leaving group and form a new carbonyl compound.

Reactivity of Aromatic Compounds

Aromatic compounds, such as toluene, exhibit unique reactivity due to their stable π-electron system. This stability allows them to undergo electrophilic aromatic substitution rather than nucleophilic reactions. However, under certain conditions, aromatic compounds can participate in nucleophilic acyl substitution, especially when activated by electron-withdrawing groups or when reacting with acyl chlorides or anhydrides.

Formation of Amides

Amides are formed when a carboxylic acid or its derivative reacts with an amine. In the context of nucleophilic acyl substitution, the amine acts as the nucleophile, attacking the carbonyl carbon of the acyl compound. This reaction is crucial in organic synthesis, as amides are important functional groups found in various natural products and pharmaceuticals.

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

Key Concepts

Nucleophilic Acyl Substitution

Reactivity of Aromatic Compounds

Formation of Amides

Watch next

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