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 Replacement Reactions

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Diazo Replacement Reactions

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3:17 minutes

Problem 39c

Textbook Question

Predict the products of the following reactions:
(c)

Verified step by step guidance

Step 1: Analyze the starting material. The molecule is a nitroaniline, specifically 2-nitroaniline, with an amino group (-NH₂) at the ortho position relative to the nitro group (-NO₂) on a benzene ring.

Step 2: Understand the reaction conditions. The first step involves sodium nitrite (NaNO₂) and hydrochloric acid (HCl), which are used to convert the amino group (-NH₂) into a diazonium salt (-N₂⁺Cl⁻). This is known as diazotization.

Step 3: Write the intermediate structure. After diazotization, the amino group is replaced by a diazonium group (-N₂⁺Cl⁻), resulting in 2-nitrobenzenediazonium chloride.

Step 4: Examine the second reagent, CuBr. Copper(I) bromide (CuBr) facilitates a Sandmeyer reaction, where the diazonium group (-N₂⁺Cl⁻) is replaced by a bromine atom (-Br). This substitution occurs via a radical mechanism.

Step 5: Predict the final product. The bromine atom replaces the diazonium group, yielding 2-nitrobromobenzene as the final product. The nitro group (-NO₂) remains unchanged during the reaction.

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Key Concepts

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

Diazotization

Diazotization is a chemical reaction that involves converting an amine group (-NH2) into a diazonium salt (-N2+). This is typically achieved by treating the amine with sodium nitrite (NaNO2) in the presence of a strong acid like hydrochloric acid (HCl). The resulting diazonium salt is a key intermediate in various organic reactions, allowing for further substitution reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of diazonium salts, the nitrogen gas (N2) leaves, and a nucleophile, such as bromide ion (Br-) from CuBr, can replace it, leading to the formation of a new compound. This reaction is crucial for introducing different functional groups into aromatic systems.

Aromatic Compounds

Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized π-electrons, which follow Huckel's rule (4n + 2 π electrons). The presence of substituents, such as -NH2 and -NO2, can influence the reactivity and stability of these compounds. Understanding the electronic effects of these substituents is essential for predicting the outcomes of reactions involving aromatic systems.

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