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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2:53 minutes

Problem 20c

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:
c.

Verified step by step guidance

Step 1: Identify the target compound, diphenyl ketone (benzophenone), which has a ketone functional group (C=O) attached to two phenyl groups (Ph). This structure suggests the use of Friedel–Crafts acylation as a key step in the synthesis.

Step 2: Select benzene (C6H6) as the starting material. Friedel–Crafts acylation involves the reaction of an aromatic compound (benzene) with an acyl chloride in the presence of a Lewis acid catalyst, such as AlCl3.

Step 3: Choose benzoyl chloride (C6H5COCl) as the acylating agent. Benzoyl chloride contains the acyl group (C6H5CO-) needed to form the ketone functional group in the target compound.

Step 4: Perform the Friedel–Crafts acylation reaction. Mix benzene with benzoyl chloride in the presence of AlCl3. The Lewis acid catalyst facilitates the generation of the electrophilic acylium ion (C6H5CO+), which reacts with benzene to form benzophenone.

Step 5: After the reaction, isolate and purify the product, diphenyl ketone (benzophenone), using standard organic chemistry techniques such as distillation or recrystallization.

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Key Concepts

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

Friedel–Crafts Acylation

Friedel–Crafts acylation is an electrophilic aromatic substitution reaction that introduces an acyl group into an aromatic ring. This reaction typically uses an acyl chloride and a Lewis acid catalyst, such as aluminum chloride, to form a ketone. The acyl group enhances the reactivity of the aromatic compound, allowing for further functionalization. Understanding this reaction is crucial for synthesizing complex aromatic compounds.

Clemmensen Reduction

The Clemmensen reduction is a chemical reaction that reduces carbonyl groups (aldehydes and ketones) to methylene groups (alkanes) using zinc amalgam and hydrochloric acid. This reaction is particularly useful in organic synthesis when the carbonyl compound is sensitive to other reducing conditions. Recognizing when to apply this reduction is essential for modifying aromatic compounds after acylation.

Gatterman–Koch Synthesis

The Gatterman–Koch synthesis is a method for introducing formyl groups into aromatic compounds via the reaction of an aromatic compound with carbon monoxide and hydrochloric acid in the presence of a Lewis acid catalyst. This reaction is significant for synthesizing aldehydes from aromatic substrates, providing a pathway to further functionalization. Mastery of this synthesis is important for constructing complex aromatic systems.