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

19. Reactions of Aromatics: EAS and Beyond

Diazo Sequence Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Diazo Sequence Groups

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3:03 minutes

Problem 32

Textbook Question

What product is formed from the reaction of p-methylphenol with benzenediazonium chloride?

Verified step by step guidance

Step 1: Recognize the type of reaction. This is an example of an electrophilic aromatic substitution reaction, specifically a diazo coupling reaction, where benzenediazonium chloride acts as an electrophile and p-methylphenol acts as a nucleophile.

Step 2: Identify the reactive site on p-methylphenol. The hydroxyl (-OH) group on the phenol ring is an activating group that increases electron density on the aromatic ring, especially at the ortho and para positions relative to the -OH group. Since the methyl group is already at the para position, the coupling will likely occur at the ortho position.

Step 3: Understand the mechanism. The diazonium ion (N≡N⁺) from benzenediazonium chloride attacks the electron-rich ortho position of p-methylphenol, forming a new bond between the aromatic ring of p-methylphenol and the diazonium group.

Step 4: Consider resonance stabilization. The resulting product will have conjugation between the aromatic ring and the azo (-N=N-) group, which stabilizes the molecule. This conjugation is responsible for the vibrant colors of azo compounds.

Step 5: Name the product. The final product is an azo compound, specifically 2-(p-methylphenylazo)-p-methylphenol, where the azo group (-N=N-) connects the p-methylphenol and the benzene ring from benzenediazonium chloride.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this context, benzenediazonium chloride acts as the electrophile, which can react with the electron-rich p-methylphenol, leading to the substitution of a hydrogen atom on the aromatic ring.

Aromatic Compounds

Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized π-electrons. p-Methylphenol, also known as p-cresol, is an aromatic compound that contains a hydroxyl group (-OH) and a methyl group (-CH3) attached to a benzene ring, influencing its reactivity in electrophilic substitution reactions.

Diazonium Salts

Diazonium salts are highly reactive intermediates in organic synthesis, formed by the reaction of primary aromatic amines with nitrous acid. Benzenediazonium chloride is a common diazonium salt that can participate in various coupling reactions, including those with aromatic compounds like p-methylphenol, resulting in the formation of azo compounds.

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