Textbook Question
Predict the major products of the following reactions.
(a) 2,4-dinitrochlorobenzene + NaOCH3
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Ch. 17 - Reactions of Aromatic Compounds
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 17, Problem 53b
Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl3
Verified step by step guidance1
Step 1: Recognize the type of reaction. This is an example of a Friedel-Crafts alkylation reaction, where an aromatic compound (phenol) reacts with an alkyl halide (tert-butyl chloride) in the presence of a Lewis acid catalyst (AlCl₃). The reaction introduces an alkyl group onto the aromatic ring.
Step 2: Understand the role of the reagents. AlCl₃ acts as a Lewis acid to generate a carbocation from tert-butyl chloride. The tert-butyl carbocation (C(CH₃)₃⁺) is a highly stable tertiary carbocation, which will act as the electrophile in this reaction.
Step 3: Consider the directing effects of the hydroxyl (-OH) group on phenol. The -OH group is an activating and ortho/para-directing group, meaning it increases the reactivity of the aromatic ring and directs the incoming electrophile to the ortho and para positions relative to itself.
Step 4: Predict the major products. The tert-butyl group will preferentially add to the para position of the phenol due to steric hindrance at the ortho positions. However, some ortho substitution may also occur as a minor product.
Step 5: Draw the structures of the products. The major product will be para-tert-butylphenol, and the minor product will be ortho-tert-butylphenol. Ensure to represent the aromatic ring with the hydroxyl group and the tert-butyl group in the correct positions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of phenol, the hydroxyl group (-OH) activates the ring, making it more reactive towards electrophiles. Understanding EAS is crucial for predicting the products of reactions involving aromatic compounds.
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EAS Review
Lewis Acids and Bases
Lewis acids are species that can accept an electron pair, while Lewis bases donate an electron pair. In this reaction, AlCl3 acts as a Lewis acid, facilitating the formation of a more reactive electrophile from tert-butyl chloride. Recognizing the role of Lewis acids and bases is essential for understanding how they influence reaction mechanisms and product formation.
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02:49The Lewis definition of acids and bases.
Regioselectivity in Substitution Reactions
Regioselectivity refers to the preference of a chemical reaction to occur at one location over another in a molecule. In the case of phenol reacting with tert-butyl chloride in the presence of AlCl3, the reaction will likely occur at the ortho or para positions due to the activating effect of the hydroxyl group. Understanding regioselectivity helps predict the major products formed in substitution reactions.
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01:34Recognizing Substitution Reactions.
Related Practice
Textbook Question
Predict the major products of the following reactions.
(d) nitrobenzene + acetyl chloride + AlCl3
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Textbook Question
Predict the major products of the following reactions.
(c) nitrobenzene + fuming sulfuric acid
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Textbook Question
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.
a. 1-phenyl-1-bromobutane
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Textbook Question
Predict the major products of the following reactions.
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Textbook Question
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.
b. 1-phenyl-1-methoxybutane
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