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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4:19 minutes

Problem 20h

Textbook Question

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

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Use Friedel–Crafts acylation to introduce an acetyl group (-COCH3) onto the benzene ring. This reaction requires an acyl chloride (CH3COCl) and a Lewis acid catalyst such as AlCl3.

Step 2: Perform a Clemmensen reduction to convert the ketone group (-COCH3) introduced in the previous step into an alkyl group (-CH2CH3). This reduction is carried out using zinc amalgam (Zn(Hg)) and concentrated hydrochloric acid (HCl).

Step 3: Introduce the amine group (-NH2) onto the benzene ring. This can be achieved by nitration of the benzene ring (using HNO3 and H2SO4) followed by reduction of the nitro group (-NO2) to an amine (-NH2) using a reducing agent such as Sn/HCl or Fe/HCl.

Step 4: Convert the amine group (-NH2) into an amide group (-NHCOCH3) by reacting it with acetic anhydride (CH3CO)2O. This step forms the first amide bond on the benzene ring.

Step 5: Finally, introduce the second amide group (-NHCOCH3) onto the benzene ring by reacting the amine group with another equivalent of acetic anhydride. This completes the synthesis of the target compound.

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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 generate the acylium ion, which then reacts with the benzene ring. This method is crucial for synthesizing aromatic ketones, which are often precursors for further functionalization.

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 for converting aromatic ketones into aliphatic compounds, making it a valuable tool in organic synthesis when other reduction methods are not suitable due to the presence of sensitive functional groups.

Gatterman–Koch Synthesis

The Gatterman–Koch synthesis is a method for synthesizing aromatic aldehydes from aromatic compounds using carbon monoxide and hydrochloric acid in the presence of a Lewis acid catalyst, typically aluminum chloride. This reaction allows for the introduction of formyl groups into aromatic rings, which can be further transformed into various functional groups, making it a versatile approach in organic synthesis.

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

Key Concepts

Friedel–Crafts Acylation

Clemmensen Reduction

Gatterman–Koch Synthesis

Watch next

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