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

26. Amines

Nitrogenous Nucleophiles

Organic Chemistry

26. Amines

Nitrogenous Nucleophiles

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1:38 minutes

Problem 55b

Textbook Question

Predict the product(s) of the reactions shown.
(b)

Verified step by step guidance

Identify the starting material: The compound is an aromatic amine, specifically an aniline derivative with a tert-butyl group attached to the benzene ring.

Understand the reaction conditions: The first step involves NaNO2 and HCl, which is used to convert the amine group into a diazonium salt. This is known as diazotization.

Write the diazotization reaction: The amine group (NH2) will be transformed into a diazonium group (N2+), forming an aryl diazonium salt. The reaction can be represented as: NH2 + NaNO2 + HCl → N2+ + Cl- + H2O.

Consider the second step: The diazonium salt reacts with CuCl, which is a Sandmeyer reaction. This reaction replaces the diazonium group with a chlorine atom.

Predict the final product: The tert-butyl group remains unchanged, and the diazonium group is replaced by a chlorine atom, resulting in a chlorinated aromatic compound.

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Key Concepts

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

Diazotization Reaction

Diazotization is a chemical reaction that converts an aromatic amine into a diazonium salt using nitrous acid, typically generated in situ from sodium nitrite and hydrochloric acid. This reaction is crucial for introducing a diazonium group, which can be further transformed into various functional groups through substitution reactions.

Sandmeyer Reaction

The Sandmeyer reaction involves the substitution of an aromatic diazonium group with a halide or pseudohalide using copper(I) salts. In this case, CuCl facilitates the replacement of the diazonium group with a chlorine atom, allowing for the synthesis of aryl chlorides from aryl amines, expanding the functional diversity of aromatic compounds.

Aromatic Substitution

Aromatic substitution refers to the replacement of a substituent on an aromatic ring with another group. In the context of the reaction shown, the diazonium group formed from the amine is substituted by a chlorine atom, demonstrating the versatility of aromatic compounds in undergoing various substitution reactions to yield different products.

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Synthesize from benzene. (Hint: All of these require diazonium ions.)

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Using any necessary reagents, show how you would accomplish the following syntheses.

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