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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Multiple Choice

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

The figure illustrates a series of four reactions to synthesize the desired product. The first reaction contains two species. The first species is H N O 3 written over the reaction arrow. The second species is H 2 S O 4 written under the reaction arrow.The second reaction contains one species. The species is H 2 written over the reaction arrow. P d over C is written under the reaction arrow.The third reaction contains two species. The first species is N a N O 2 written over the reaction arrow. The second species is H C l written under the reaction arrow.The fourth reaction contains one species. The species is C u C N written over the reaction arrow.

The figure illustrates a series of two reactions to synthesize the desired product. The first reaction contains two species. The first species is B r 2 written over the reaction arrow. The second species is F e B r 3 written under the reaction arrow.The second reaction contains one species. The species is N a C N written over the reaction arrow. T H F is written under the reaction arrow.

The figure illustrates the reagents used to synthesize the desired product. The reaction contains two species. The first species is C l C N written over the reaction arrow. The second species is A l C l 3 written under the reaction arrow.

The figure illustrates a series of three reactions to synthesize the desired product. The first reaction contains two species. The first species is M e B r written over the reaction arrow. The second species is F e B r 3 written under the reaction arrow.The second reaction contains one species. The species is N B S written over the reaction arrow. h nu is written under the reaction arrow.The third reaction contains one species. The species is N a C N written over the reaction arrow. T H F is written under the reaction arrow.

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Verified step by step guidance

Identify the target molecule as benzonitrile, which is benzene with a cyano group (CN) attached.

Consider the first reaction sequence: Nitration of benzene using HNO3 and H2SO4 to form nitrobenzene, reduction of nitrobenzene to aniline using H2 and Pd/C, diazotization of aniline with NaNO2 and HCl to form a diazonium salt, and finally, Sandmeyer reaction with CuCN to replace the diazonium group with a cyano group.

Evaluate the second reaction sequence: Bromination of benzene using Br2 and FeBr3 to form bromobenzene, followed by nucleophilic substitution with NaCN in THF to replace the bromine with a cyano group.

Analyze the third reaction sequence: Friedel-Crafts acylation using ClCN and AlCl3, which is not a typical method for introducing a cyano group directly onto benzene.

Review the fourth reaction sequence: Methylation of benzene using MeBr and FeBr3, followed by bromination of the methyl group using NBS and light (hν) to form benzyl bromide, and finally, nucleophilic substitution with NaCN in THF to form benzonitrile.