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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7:24 minutes

Problem 52f

Textbook Question

Show how the following compounds can be synthesized from benzene:
f. m-hydroxybenzoic acid

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Perform a nitration reaction by treating benzene with a mixture of concentrated HNO₃ and H₂SO₄. This introduces a nitro group (-NO₂) onto the benzene ring, forming nitrobenzene.

Step 2: Reduce the nitro group (-NO₂) in nitrobenzene to an amino group (-NH₂) using a reducing agent such as Sn/HCl or Fe/HCl. This forms aniline.

Step 3: Protect the amino group (-NH₂) by acetylation. React aniline with acetic anhydride to form acetanilide. This step prevents unwanted reactions during subsequent steps.

Step 4: Perform a Friedel-Crafts acylation reaction on acetanilide using CO₂ and AlCl₃ to introduce a carboxylic acid group (-COOH) in the meta position relative to the protected amino group. This forms m-acetylaminobenzoic acid.

Step 5: Hydrolyze the acetanilide group under acidic or basic conditions to remove the acetyl group and regenerate the amino group. Then oxidize the amino group to a hydroxyl group (-OH) using a suitable oxidizing agent, such as NaNO₂/HCl, to yield m-hydroxybenzoic acid.

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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 substituted aromatic compounds, such as m-hydroxybenzoic acid from benzene. Understanding the mechanism of EAS, including the role of the electrophile and the stability of the carbocation intermediate, is essential for predicting the products of reactions involving benzene derivatives.

Ortho/Para vs. Meta Directing Groups

In electrophilic aromatic substitution, substituents on the benzene ring can influence the position of further substitutions. Ortho and para directing groups favor substitution at the 2 and 4 positions, while meta directing groups lead to substitution at the 3 position. Recognizing the directing effects of functional groups, such as hydroxyl (-OH) and carboxylic acid (-COOH), is vital for determining the correct synthesis pathway for m-hydroxybenzoic acid.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through various chemical reactions. In the synthesis of m-hydroxybenzoic acid, the transformation of a nitrile (-CN) group into a carboxylic acid (-COOH) is a key step. Familiarity with common reactions, such as hydrolysis of nitriles, is necessary to understand how to achieve the desired functional groups in the final product.

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