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 75a
Show how the following compounds can be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
a. 
Verified step by step guidance1
Step 1: Begin with the starting material, toluene (C6H5CH3). The methyl group on the benzene ring will serve as the site for functionalization.
Step 2: Perform a benzylic oxidation of the methyl group using a strong oxidizing agent such as KMnO4 or Na2Cr2O7 under acidic conditions. This will convert the methyl group (-CH3) into a carboxylic acid group (-COOH), yielding benzoic acid (C6H5COOH).
Step 3: Convert the benzoic acid into an acid chloride (-COCl) by treating it with thionyl chloride (SOCl2). This reaction replaces the hydroxyl group (-OH) of the carboxylic acid with a chlorine atom, forming benzoyl chloride (C6H5COCl).
Step 4: React the benzoyl chloride with ethylamine (CH3CH2NH2) in the presence of a base such as pyridine. This nucleophilic acyl substitution will replace the chlorine atom with the ethylamine group, forming the desired amide product, N-ethylbenzamide (C6H5CONHCH2CH3).
Step 5: Purify the final product using standard organic purification techniques such as recrystallization or chromatography to ensure the desired compound is obtained in high purity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an acyl compound, leading to the replacement of a leaving group with the nucleophile. In this process, the carbonyl carbon becomes electrophilic, allowing the nucleophile to form a tetrahedral intermediate, which then collapses to release the leaving group and form a new carbonyl compound.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Reactivity of Aromatic Compounds
Aromatic compounds, such as toluene, exhibit unique reactivity due to their stable π-electron system. This stability allows them to undergo electrophilic aromatic substitution rather than nucleophilic reactions. However, under certain conditions, aromatic compounds can participate in nucleophilic acyl substitution, especially when activated by electron-withdrawing groups or when reacting with acyl chlorides or anhydrides.
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Formation of Amides
Amides are formed when a carboxylic acid or its derivative reacts with an amine. In the context of nucleophilic acyl substitution, the amine acts as the nucleophile, attacking the carbonyl carbon of the acyl compound. This reaction is crucial in organic synthesis, as amides are important functional groups found in various natural products and pharmaceuticals.
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Related Practice
Textbook Question
b. Describe two ways the following reaction can be carried out:
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Textbook Question
Rank the following compounds from largest Keq to smallest Keq for hydrate formation:
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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
a. Describe three ways the following reaction can be carried out:
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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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