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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5:23 minutes

Problem 23a

Textbook Question

Show how the following compounds can be synthesized from benzene:
a.

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Benzene is a simple aromatic compound with a six-membered ring and alternating double bonds.

Step 2: Perform a nitration reaction to introduce a nitro group (-NO₂) onto the benzene ring. This is achieved by treating benzene with a mixture of concentrated nitric acid (HNO₃) and concentrated sulfuric acid (H₂SO₄). The nitro group will attach to the benzene ring, forming nitrobenzene.

Step 3: Carry out a Friedel-Crafts acylation reaction to introduce the acetyl group (-COCH₃) onto the benzene ring. This is done by reacting nitrobenzene with acetyl chloride (CH₃COCl) in the presence of a Lewis acid catalyst, such as aluminum chloride (AlCl₃). The acetyl group will attach to the benzene ring, forming the desired compound.

Step 4: Ensure that the nitro group and acetyl group are positioned correctly on the benzene ring. The nitro group is meta-directing, meaning that the acetyl group will preferentially attach to the meta position relative to the nitro group during the Friedel-Crafts acylation.

Step 5: Verify the structure of the final product, which should be 3-nitroacetophenone. This compound has a nitro group (-NO₂) at the meta position and an acetyl group (-COCH₃) attached to 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, such as benzene. This process is crucial for synthesizing various compounds from benzene, as it allows for the introduction of different functional groups while preserving the aromaticity of the ring.

Reagents and Conditions

Different reagents and conditions are required for specific electrophilic aromatic substitution reactions. For example, the use of halogens with a Lewis acid catalyst can facilitate halogenation, while nitration requires a mixture of concentrated nitric and sulfuric acids. Understanding the appropriate reagents and conditions is essential for successfully synthesizing target compounds from benzene.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through various chemical reactions. In the context of synthesizing compounds from benzene, this may include processes like reduction, oxidation, or rearrangement after initial substitution. Mastery of these transformations is vital for achieving the desired final products in organic synthesis.

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