Textbook Question
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
c. n-butylbenzene
681
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Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 21, Problem 30b
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
b. benzophenone
Verified step by step guidance1
Step 1: Understand the Friedel–Crafts acylation reaction. This reaction involves the introduction of an acyl group (RCO-) into an aromatic ring using an acyl chloride (RCOCl) and a Lewis acid catalyst, typically aluminum chloride (AlCl₃). The reaction proceeds via electrophilic aromatic substitution.
Step 2: Identify the target compound, benzophenone. Benzophenone has two phenyl groups attached to a carbonyl group (C=O). This means one phenyl group will act as the aromatic ring undergoing acylation, while the other phenyl group will be part of the acyl group.
Step 3: Choose the appropriate acylating agent. To synthesize benzophenone, the acylating agent should be benzoyl chloride (C₆H₅COCl), which contains the phenyl group attached to the carbonyl group.
Step 4: Set up the reaction. Combine benzene (C₆H₆) as the aromatic substrate with benzoyl chloride (C₆H₅COCl) in the presence of a Lewis acid catalyst, such as AlCl₃. The AlCl₃ activates the benzoyl chloride by forming a complex, making the carbonyl carbon more electrophilic and susceptible to attack by the benzene ring.
Step 5: Complete the reaction mechanism. The benzene ring donates electrons to the electrophilic carbonyl carbon, forming a sigma complex. The AlCl₃ catalyst helps stabilize the intermediate, and a proton is lost to regenerate the aromaticity of the benzene ring. The final product is benzophenone (C₆H₅COC₆H₅).
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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 involves the use of an acyl chloride and a Lewis acid catalyst, such as aluminum chloride, to generate the acylium ion, which then reacts with the aromatic compound. This method is valuable for synthesizing ketones from aromatic compounds.
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Friedel-Crafts Acylation
Benzophenone Structure
Benzophenone is an organic compound characterized by two phenyl groups attached to a carbonyl group (C=O). Its structure can be represented as Ph-CO-Ph, where 'Ph' denotes a phenyl group. Understanding the structure of benzophenone is crucial for recognizing how Friedel–Crafts acylation can be applied to synthesize it from simpler aromatic precursors.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is essential for the synthesis of various aromatic compounds, including benzophenone. The stability of the aromatic system is maintained during the reaction, making EAS a key concept in understanding how acylation can modify aromatic compounds.
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Related Practice
Textbook Question
Show how you would add a Grignard reagent to an ester or a nitrile to synthesize
(c) pentan-2-one.
706
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Textbook Question
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(c) phthalic acid monoamide
(d) succinic acid monomethyl ester
597
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Textbook Question
Show how you would add a Grignard reagent to an ester or a nitrile to synthesize
(b) heptan-4-ol.
598
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Textbook Question
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
a. acetophenone
1313
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Textbook Question
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(a) n-octyl formate
(b) n-octyl acetate
1211
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