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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5:42 minutes

Problem 80c

Textbook Question

How can you prepare the following compounds with benzene as one of the starting materials?
c.

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Perform a Friedel-Crafts acylation reaction using succinic anhydride (C4H4O3) and a Lewis acid catalyst such as AlCl3. This introduces a four-carbon chain with a ketone group onto the benzene ring.

Step 2: The product from Step 1 will be benzoyl succinic acid. Cyclize this intermediate by heating it under acidic conditions to form a cyclic ketone structure. This step involves intramolecular aldol condensation.

Step 3: Perform a second Friedel-Crafts acylation reaction using another equivalent of succinic anhydride and AlCl3. This introduces another four-carbon chain with a ketone group onto the benzene ring.

Step 4: Cyclize the second intermediate under acidic conditions to form the second cyclic ketone structure. This step involves another intramolecular aldol condensation.

Step 5: The final product is the compound shown in the image, which contains two fused cyclic ketone structures 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 (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring, such as benzene. This reaction is crucial for synthesizing various substituted aromatic compounds. The process typically involves the generation of a highly reactive electrophile, which then attacks the electron-rich aromatic system, leading to the formation of a sigma complex before restoring aromaticity.

Aromaticity

Aromaticity refers to the special stability and reactivity of certain cyclic compounds that contain conjugated pi electron systems, such as benzene. For a compound to be aromatic, it must follow Hückel's rule, which states that it should have 4n + 2 pi electrons (where n is a non-negative integer). This property is essential for understanding why benzene and its derivatives undergo substitution reactions rather than addition reactions.

Substituent Effects

Substituent effects are the influences that different groups attached to an aromatic ring have on the reactivity and orientation of electrophilic substitution reactions. Electron-donating groups (EDGs) activate the ring and direct incoming electrophiles to ortho and para positions, while electron-withdrawing groups (EWGs) deactivate the ring and direct electrophiles to the meta position. Understanding these effects is vital for predicting the outcomes of reactions involving substituted aromatic compounds.

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