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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1:45 minutes

Problem 48d

Textbook Question

Draw the product(s) of each of the following reactions:
d. o-methylaniline + benzenediazonium chloride

Verified step by step guidance

Identify the type of reaction: This is an electrophilic aromatic substitution reaction, specifically an azo coupling reaction. Benzenediazonium chloride acts as an electrophile, and o-methylaniline (an aromatic amine) acts as the nucleophile.

Determine the directing effects of the substituents on o-methylaniline: The -NH2 group (amino group) is an electron-donating group and strongly activates the aromatic ring, directing substitution to the ortho and para positions relative to itself. The -CH3 group (methyl group) is also electron-donating but weaker, and it will not significantly affect the reaction compared to the -NH2 group.

Predict the site of electrophilic attack: Since the -NH2 group is the strongest activator, the azo coupling will occur at the para position relative to the -NH2 group. However, the ortho position relative to the -NH2 group is already occupied by the -CH3 group, so the para position is the most favorable site for the reaction.

Draw the product structure: The product will be an azo compound where the diazonium group (-N≡N⁺) from benzenediazonium chloride couples with the para position of o-methylaniline. The resulting structure will have the -N=N- group connecting the benzene ring of benzenediazonium chloride to the aromatic ring of o-methylaniline.

Verify the stability of the product: Azo compounds are generally stable, and the electron-donating -NH2 group on o-methylaniline further stabilizes the product by resonance. Ensure the final structure reflects the correct connectivity and substituents.

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Key Concepts

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

Aromatic Substitution Reactions

Aromatic substitution reactions involve the replacement of a hydrogen atom in an aromatic ring with another atom or group. This process is crucial in organic chemistry, particularly in reactions involving electrophiles and nucleophiles. In the case of o-methylaniline and benzenediazonium chloride, the reaction exemplifies electrophilic aromatic substitution, where the diazonium ion acts as an electrophile.

Diazonium Compounds

Diazonium compounds are highly reactive intermediates in organic synthesis, characterized by the presence of a diazonium group (-N2+). They are typically formed from primary aromatic amines and are used to introduce various substituents onto aromatic rings. In this reaction, benzenediazonium chloride serves as the electrophile that will react with o-methylaniline to form a new aromatic compound.

Ortho and Para Substitution

In electrophilic aromatic substitution, the position of the new substituent on the aromatic ring can be ortho (adjacent) or para (opposite) to the original substituent. The directing effects of substituents, such as the amino group in o-methylaniline, influence the outcome of the reaction. In this case, the amino group is an ortho/para director, leading to the formation of products at these positions.

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