Textbook Question
What products are obtained from the reaction of the following compounds with H2CrO4 + ∆?
b.
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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 70(c)
What are the products of the following reactions?
c. 
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a Friedel-Crafts acylation reaction, where an aromatic compound reacts with an acyl chloride in the presence of a Lewis acid catalyst (AlCl₃).
Step 2: Identify the reactants. The aromatic compound is benzene, and the acyl chloride is benzoyl chloride (C₆H₅COCl). The catalyst is aluminum chloride (AlCl₃).
Step 3: Understand the mechanism. The AlCl₃ catalyst interacts with the acyl chloride to form a highly electrophilic acylium ion (C₆H₅CO⁺), which is the active species in the reaction.
Step 4: Predict the electrophilic aromatic substitution. The acylium ion attacks the benzene ring, leading to the formation of a new carbon-carbon bond. This results in the substitution of a hydrogen atom on the benzene ring with the acyl group (C₆H₅CO).
Step 5: Finalize the product. The product of this reaction is acetophenone (C₆H₅COC₆H₆), where the benzene ring is bonded to the carbonyl group of the acyl chloride. The AlCl₃ catalyst is regenerated at the end of the reaction.
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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 where an acyl group is introduced into an aromatic ring. This reaction typically involves the use of an acyl chloride and a Lewis acid catalyst, such as aluminum chloride (AlCl3), which activates the acyl chloride to form a more reactive acylium ion. The acylium ion then reacts with the aromatic compound, resulting in the formation of a ketone substituted on the aromatic ring.
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Friedel-Crafts Acylation
Electrophilic Aromatic Substitution (EAS)
Electrophilic aromatic substitution is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The aromatic system's electron-rich nature allows it to react with electrophiles, leading to the formation of a new carbon-electrophile bond. This mechanism is crucial for understanding various reactions involving aromatic compounds, including Friedel-Crafts reactions.
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Role of Lewis Acids
Lewis acids are substances that can accept an electron pair from a Lewis base, facilitating various chemical reactions. In the context of Friedel-Crafts acylation, aluminum chloride (AlCl3) acts as a Lewis acid by coordinating with the acyl chloride, enhancing its electrophilicity. This interaction is essential for generating the acylium ion, which is the active electrophile that reacts with the aromatic compound.
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Related Practice
Textbook Question
What are the products of the following reactions?
b.
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Textbook Question
Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acyl chloride was used in the Friedel–Crafts acylation?
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Textbook Question
What are the products of the following reactions?
a.
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Textbook Question
What are the products of the following reactions?
c.
Textbook Question
Which set of underlined hydrogens has its 1H NMR signal at a higher frequency?
a. CH3CH2CH3 or CH3OCH2CH3
b. CH3CH=CH2 or CH3OCH=CH2
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