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

EAS:Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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2:44 minutes

Problem 24d

Textbook Question

Show how each of the following compounds can be synthesized from benzene:
d. p-chloroaniline

Verified step by step guidance

Step 1: Begin with benzene as the starting material. The first step is to introduce a chlorine atom onto the benzene ring. This can be achieved through an electrophilic aromatic substitution reaction called chlorination. React benzene with chlorine (Cl₂) in the presence of a catalyst such as FeCl₃ to form chlorobenzene. The reaction is:

C 6_{6} H 6_{6} + {Cl}_{2} → C_{6} H_{5} Cl

Step 2: Next, introduce the amino group (-NH₂) onto the benzene ring. To achieve this, perform a nitration reaction on chlorobenzene. React chlorobenzene with a mixture of concentrated nitric acid (HNO₃) and sulfuric acid (H₂SO₄) to form p-nitrochlorobenzene. This reaction introduces a nitro group (-NO₂) at the para position relative to the chlorine atom due to the electron-withdrawing nature of the chlorine substituent.

Step 3: Reduce the nitro group (-NO₂) in p-nitrochlorobenzene to an amino group (-NH₂). This can be done using a reducing agent such as tin (Sn) and hydrochloric acid (HCl), followed by neutralization with a base. The product of this step is p-chloroaniline.

Step 4: Purify the p-chloroaniline product to ensure it is free of any by-products or impurities. This can be done through recrystallization or other purification techniques.

Step 5: Verify the structure of the synthesized p-chloroaniline using spectroscopic methods such as IR, NMR, or mass spectrometry to confirm the presence of the desired functional groups and the correct substitution pattern 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.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for synthesizing various derivatives of benzene, including p-chloroaniline. Understanding the mechanism of EAS helps in predicting the positions where substituents will attach to the aromatic ring based on the directing effects of existing groups.

Nitration of Benzene

Nitration is a specific type of electrophilic aromatic substitution where a nitro group (NO2) is introduced to the benzene ring. This reaction typically involves the use of concentrated nitric acid and sulfuric acid. The resulting nitrobenzene can then be further transformed into p-chloroaniline through subsequent reactions, highlighting the importance of nitration in the synthesis pathway.

Reduction of Nitro Compounds

The reduction of nitro compounds is a key step in converting nitrobenzene to an amine, such as p-chloroaniline. This process can be achieved using various reducing agents, such as iron and hydrochloric acid or catalytic hydrogenation. Understanding the reduction mechanism is essential for successfully synthesizing amines from their corresponding nitro derivatives, which is a critical step in the overall synthesis from benzene.

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