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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7:29 minutes

Problem 23d

Textbook Question

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(d) aniline

Verified step by step guidance

Step 1: Recognize the functional group in aniline. Aniline is an aromatic amine with the structure C₆H₅NH₂, where the amino group (-NH₂) is directly attached to a benzene ring.

Step 2: Understand the reaction conditions. Sodium nitrite (NaNO₂) in dilute HCl generates nitrous acid (HNO₂) in situ. This is a key reagent for diazotization reactions, which occur with primary aromatic amines like aniline.

Step 3: Write the diazotization reaction. The amino group (-NH₂) of aniline reacts with nitrous acid (HNO₂) under acidic conditions to form a diazonium salt. The reaction can be represented as: C₆H₅NH₂ + HNO₂ + HCl → C₆H₅N₂⁺Cl⁻ + 2H₂O.

Step 4: Identify the product. The product of this reaction is benzenediazonium chloride (C₆H₅N₂⁺Cl⁻), which is a diazonium salt. This compound is highly reactive and can undergo further reactions, depending on the conditions.

Step 5: Note the importance of temperature. Diazotization reactions are typically carried out at low temperatures (0–5°C) to stabilize the diazonium salt and prevent its decomposition.

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Key Concepts

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

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Aniline, specifically, is a primary aromatic amine where the amino group (-NH2) is directly attached to a benzene ring.

Diazotization

Diazotization is a chemical reaction that involves the conversion of primary amines into diazonium salts by treatment with nitrous acid (generated in situ from sodium nitrite and hydrochloric acid). This reaction is crucial in organic synthesis, particularly for the preparation of azo compounds, which are important in dye chemistry. In the case of aniline, the amino group reacts with nitrous acid to form benzenediazonium chloride.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The presence of the amino group in aniline activates the benzene ring towards electrophilic attack, making it more reactive. After diazotization, the diazonium salt can undergo further reactions, such as substitution with nucleophiles, leading to various aromatic derivatives.

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