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:Friedel-Crafts Acylation Mechanism

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Friedel-Crafts Acylation Mechanism

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5:10 minutes

Problem 59

Textbook Question

Show two pairs of reagents that would each result in formation of the following compound:

Verified step by step guidance

Step 1: Analyze the target compound. The structure contains a ketone group (C=O) attached to two aromatic rings: one is a benzene ring, and the other is a methyl-substituted benzene ring (toluene). This suggests the compound can be synthesized via a Friedel-Crafts acylation reaction.

Step 2: Identify the acyl group. The ketone group indicates the presence of a benzoyl group (C6H5CO-) attached to the methyl-substituted benzene ring. This implies that the acylating agent could be benzoyl chloride (C6H5COCl).

Step 3: Pair 1 of reagents: Use benzoyl chloride (C6H5COCl) as the acylating agent and methylbenzene (toluene, C6H5CH3) as the aromatic substrate. Combine these reagents in the presence of a Lewis acid catalyst, such as aluminum chloride (AlCl3), to facilitate the Friedel-Crafts acylation reaction.

Step 4: Pair 2 of reagents: Alternatively, use benzoic acid (C6H5COOH) as the acylating agent and methylbenzene (toluene, C6H5CH3) as the aromatic substrate. In this case, the reaction can be carried out using a dehydrating agent like phosphorus pentoxide (P2O5) or thionyl chloride (SOCl2) to convert the benzoic acid into an acylating intermediate.

Step 5: Ensure reaction conditions are optimized. For both pairs of reagents, maintain anhydrous conditions to prevent side reactions. Monitor the reaction progress using techniques like thin-layer chromatography (TLC) to confirm the formation of the desired ketone product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Reagents in Organic Synthesis

Reagents are substances that participate in a chemical reaction to form new products. In organic synthesis, selecting the right reagents is crucial for achieving the desired transformation. Understanding the reactivity and compatibility of different reagents allows chemists to design effective synthetic pathways to create specific compounds.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups present in the target compound is essential for determining which reagents can be used to synthesize it. This knowledge helps in predicting the reactivity and interactions of the compound during the synthesis process.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how a chemical reaction occurs, detailing the bond-breaking and bond-forming processes. Understanding reaction mechanisms is vital for predicting the outcomes of reactions and for designing synthetic routes. By analyzing mechanisms, chemists can identify alternative reagents that may lead to the same product through different pathways.

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