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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8:13 minutes

Problem 102b

Textbook Question

Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin, and Nuprin. How can ibuprofen be synthesized from benzene?

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Benzene is an aromatic compound with a six-membered ring and alternating double bonds. The first step is to introduce an alkyl group onto the benzene ring through Friedel-Crafts alkylation. Use isobutyl chloride (CH3CH(CH3)CH2Cl) and a Lewis acid catalyst such as AlCl3 to attach the isobutyl group to the benzene ring.

Step 2: Oxidize the alkyl group on the benzene ring to form a carboxylic acid. This can be achieved using an oxidizing agent such as potassium permanganate (KMnO4) or chromic acid (H2CrO4). The isobutyl group will be converted into a carboxylic acid (-COOH) group.

Step 3: Introduce the second alkyl group (propyl group) onto the benzene ring. This can be done through another Friedel-Crafts alkylation reaction using propyl chloride (CH3CH2CH2Cl) and AlCl3 as the catalyst. Ensure that the substitution occurs at the correct position relative to the carboxylic acid group to match the structure of ibuprofen.

Step 4: Perform a stereoselective reaction to introduce the hydroxyl group (-OH) at the alpha position of the carboxylic acid group. This step may involve enantioselective synthesis using chiral catalysts or reagents to ensure the correct stereochemistry of ibuprofen.

Step 5: Purify the final product to obtain ibuprofen. This may involve recrystallization or chromatography to isolate ibuprofen from any side products or impurities formed during the synthesis process.

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Key Concepts

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

Aromatic Compounds

Aromatic compounds, like benzene, are characterized by their stable ring structure and delocalized π-electrons. This stability allows for specific reactions, such as electrophilic substitution, which are crucial for synthesizing more complex molecules like ibuprofen from benzene.

Electrophilic Substitution Reactions

Electrophilic substitution reactions are a key mechanism in organic chemistry where an electrophile replaces a hydrogen atom in an aromatic compound. This process is essential for modifying benzene to introduce functional groups that will ultimately lead to the synthesis of ibuprofen.

Functional Group Transformations

Functional group transformations involve changing one functional group into another, which is vital in organic synthesis. In the case of ibuprofen, converting the introduced groups from the benzene derivative into the carboxylic acid and isobutyl groups is necessary to achieve the final structure of the drug.

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Related Practice

Textbook Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

a. How can tyramine be prepared from b-phenylethylamine?

Open Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

b. How can dopamine be prepared from tyramine?

Open Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

c. Give two ways to prepare b-phenylethylamine from b-phenylethyl chloride.

Open Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

d. How can b-phenylethylamine be prepared from benzyl chloride?

Textbook Question

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

a. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion, CH3C≡O+. Be careful to draw all the resonance structures of the intermediate.

Textbook Question

Suggest a synthesis of each of the molecules shown beginning with benzene.

(c)

Textbook Question

Acetohexamide is used to treat type 2 diabetes that cannot be well controlled by diet alone. Fill in the blanks of the synthetic scheme used to synthesize acetohexamide. [Hints have been provided below each step.]

Textbook Question

Predict the product(s) of each of the following multistep reactions.

(b)

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