Textbook Question
Acetaminophen is the active ingredient in Tylenol. How can acetominophen be synthesized from benzene?
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 19, Problem 102b
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 guidance1
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.
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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.
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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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