Textbook Question
Predict the mononitration products of the following compounds.
e. m-cresol (m-methylphenol)
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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 17c
Predict the products (if any) of the following reactions.
a. (excess) benzene + isobutyl chloride + AlCl3
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a Friedel-Crafts alkylation reaction, where an alkyl halide reacts with an aromatic compound (benzene) in the presence of a Lewis acid catalyst (AlCl3 or FeCl3).
Step 2: Understand the role of the catalyst. FeCl3 acts as a Lewis acid, accepting a lone pair from the chlorine atom in isobutyl chloride, forming a carbocation intermediate.
Step 3: Analyze the carbocation formation. Isobutyl chloride forms a primary carbocation initially, but due to carbocation rearrangement, it will rearrange to a more stable tertiary carbocation.
Step 4: Predict the electrophilic substitution. The tertiary carbocation acts as the electrophile and reacts with benzene, leading to the formation of an alkylbenzene product. The benzene ring donates electrons to the carbocation, forming a sigma complex, which then loses a proton to restore aromaticity.
Step 5: Consider the excess benzene. Since benzene is in excess, the reaction will likely produce a mono-substituted product (tert-butylbenzene) rather than polysubstitution, as steric hindrance prevents further substitution.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this process, the aromatic system retains its stability while allowing for the introduction of new substituents. The reaction typically involves the formation of a sigma complex, followed by deprotonation to restore aromaticity.
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EAS Review
Lewis Acids and Catalysis
Lewis acids, such as AlCl3, are compounds that can accept an electron pair from a Lewis base, facilitating reactions by generating more reactive electrophiles. In the context of EAS, AlCl3 activates alkyl halides like isobutyl chloride, allowing them to form a more potent electrophile that can effectively react with the aromatic ring. This catalytic role is crucial for enhancing the reaction rate and product yield.
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Regioselectivity in Substitution Reactions
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In EAS reactions, the nature of the substituents already present on the aromatic ring influences where new substituents will attach. For example, alkyl groups are generally ortho/para-directing, meaning they favor substitution at the ortho or para positions relative to themselves.
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Related Practice
Textbook Question
Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:
e. 3-methyl-1-phenylbutane
Textbook Question
For each reaction, show the generation of the electrophile and predict the products.
c. tert-butylbenzene + 2-methylpropene + HF
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Textbook Question
Predict the products (if any) of the following reactions.
b. (excess) toluene + butan-1-ol + BF3
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Textbook Question
For each reaction, show the generation of the electrophile and predict the products.
d. propan-2-ol + toluene + BF3
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Textbook Question
Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.
(d) Reagents: benzamide (PhCONH2) + CH3CH2Cl
Desired Product: p-ethylbenzamide
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