Textbook Question
Show how you would accomplish the following syntheses.
(b) benzonitrile → propiophenone
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Ch. 18 - Ketones and Aldehydes
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 18, Problem 60a
Show how you would accomplish the following syntheses.
(a) benzene → n-butylbenzene
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. To introduce an alkyl group onto the benzene ring, use the Friedel-Crafts alkylation reaction. This reaction requires an alkyl halide and a Lewis acid catalyst.
Step 2: Select the appropriate alkyl halide for the desired product. In this case, n-butylbenzene requires the introduction of a straight-chain butyl group. Use 1-chlorobutane (CH₃CH₂CH₂CH₂Cl) as the alkyl halide.
Step 3: Use a Lewis acid catalyst, such as aluminum chloride (AlCl₃), to facilitate the Friedel-Crafts alkylation reaction. The catalyst helps generate a carbocation intermediate from the alkyl halide.
Step 4: Perform the reaction by mixing benzene, 1-chlorobutane, and AlCl₃ under controlled conditions. The benzene will act as a nucleophile and attack the carbocation intermediate, forming n-butylbenzene.
Step 5: After the reaction is complete, perform a workup to isolate the product. This typically involves quenching the reaction mixture with water or dilute acid to deactivate the catalyst and then purifying the product using techniques like distillation or recrystallization.
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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. This process is crucial for synthesizing substituted aromatic compounds, such as converting benzene to n-butylbenzene. Understanding the mechanism of EAS, including the formation of the sigma complex and the role of catalysts, is essential for predicting the outcome of such reactions.
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Alkylation of Aromatic Compounds
Alkylation involves the introduction of an alkyl group into an aromatic compound, typically through a Friedel-Crafts alkylation reaction. In this process, benzene reacts with an alkyl halide in the presence of a Lewis acid catalyst, such as aluminum chloride, to form the desired alkyl-substituted aromatic compound. Recognizing the conditions and limitations of this reaction is vital for successfully synthesizing n-butylbenzene from benzene.
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Rearrangement and Side Reactions
When performing alkylation reactions, it is important to consider potential rearrangements and side reactions that can occur. For example, the carbocation formed during the reaction may rearrange to a more stable structure, leading to different products. Understanding these possibilities helps in predicting the major product and optimizing reaction conditions to favor the desired synthesis of n-butylbenzene.
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Related Practice
Textbook Question
The Wittig reaction is useful for placing double bonds in less stable positions. For example, the following transformation is easily accomplished using a Wittig reaction.
(a) Show how you would use a Wittig reaction to do this.
(b) Show how you might do this without using a Wittig reaction, and then explain why the Wittig reaction is a much better synthesis.
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Textbook Question
Both NaBH4 and NaBD4 are commercially available, and D2O is common and inexpensive. Show how you would synthesize the following labeled compounds, starting with butan-2-one.
(a)
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Textbook Question
Show how you would accomplish the following syntheses.
(c) benzene → p-methoxybenzaldehyde
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Textbook Question
When LiAlH4 reduces 3-methylcyclopentanone, the product mixture contains 60% cis-3-methylcyclopentanol and 40% trans-3-methylcyclopentanol. Use your models, and make three-dimensional drawings to explain this preference for the cis isomer.
Textbook Question
Show how you would accomplish the following syntheses.
(d)
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