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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Problem 57a

Textbook Question

Predict the products of the following reactions.
(a)

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Identify the starting material: The given compound is a brominated aniline derivative with a methyl group on the benzene ring.

Recognize the reaction type: The reaction involves diazotization followed by a substitution reaction. The first step uses NaNO2 and HCl to convert the amine group (NH2) into a diazonium salt.

Write the diazotization reaction: The amine group reacts with NaNO2 and HCl to form an aryl diazonium ion (N2+), releasing water as a byproduct.

Consider the substitution step: The diazonium ion is highly reactive and can be replaced by other nucleophiles. In this case, KI is used to replace the diazonium group with an iodine atom.

Predict the final product: The final product will have the iodine atom in place of the original amine group, while the bromine and methyl groups remain unchanged on the benzene ring.

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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 substituent. These reactions typically occur via electrophilic aromatic substitution (EAS), where an electrophile attacks the electron-rich aromatic system. Understanding the mechanism of EAS is crucial for predicting the products of reactions involving aromatic compounds.

Diazotization

Diazotization is a process where primary amines are converted into diazonium salts using nitrous acid (generated from sodium nitrite and hydrochloric acid). This reaction is significant in organic synthesis as diazonium salts can undergo further reactions, such as nucleophilic substitution, to form various aromatic compounds. Recognizing the role of diazonium intermediates is essential for predicting the final products.

Nucleophilic Substitution

Nucleophilic substitution is a reaction where a nucleophile replaces a leaving group in a molecule. In the context of the provided reaction, the iodide ion (from KI) acts as a nucleophile that replaces the bromine atom in the diazonium compound. Understanding the conditions and mechanisms of nucleophilic substitution helps in predicting the outcome of reactions involving halogenated aromatic compounds.

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Related Practice

Textbook Question

Show how you would convert aniline to the following compounds.

(a) fluorobenzene

(b) chlorobenzene

Textbook Question

Predict the products of the following reactions:

(c)

Textbook Question

Show how you would convert aniline to the following compounds.

(d) bromobenzene

(e) iodobenzene

Textbook Question

Show how you would convert aniline to the following compounds.

(f) benzonitrile

Multiple Choice

Which of the following successfully synthesizes the given target, starting with unsubstituted benzene?

Textbook Question

In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?

Textbook Question

a. Explain why the following reaction leads to the products shown:

Textbook Question

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.

(d) aniline

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