Textbook Question
Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.
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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 96
Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.
Verified step by step guidance1
Step 1: Begin with benzene (C₆H₆) as the starting material. Perform a Friedel-Crafts acylation reaction using acetyl chloride (CH₃COCl) and aluminum chloride (AlCl₃) as the catalyst. This will introduce an acetyl group (-COCH₃) onto the benzene ring, forming acetophenone (C₆H₅COCH₃).
Step 2: Reduce the carbonyl group in acetophenone to a secondary alcohol. Use a reducing agent such as sodium borohydride (NaBH₄) in a suitable solvent like ethanol. This will convert acetophenone into 1-phenylethanol (C₆H₅CH(OH)CH₃).
Step 3: Prepare a Grignard reagent using bromoethane (C₂H₅Br) and magnesium (Mg) in anhydrous ether. This will form ethylmagnesium bromide (C₂H₅MgBr), which is a nucleophilic reagent.
Step 4: React the Grignard reagent (C₂H₅MgBr) with 1-phenylethanol. The Grignard reagent will attack the carbonyl carbon of the alcohol, forming a tertiary alcohol. This step will yield 3-methyl-1-phenyl-3-pentanol (C₆H₅CH(OH)CH₂CH(CH₃)CH₃) after hydrolysis with water or dilute acid.
Step 5: Purify the final product, 3-methyl-1-phenyl-3-pentanol, using standard organic purification techniques such as distillation or recrystallization, depending on the physical properties of the compound.
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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 context of preparing 3-methyl-1-phenyl-3-pentanol from benzene, EAS allows for the introduction of functional groups onto the benzene ring, which is crucial for building the desired compound. Common electrophiles used in this process include alkyl halides and acyl chlorides.
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Grignard Reagents
Grignard reagents are organomagnesium compounds that act as nucleophiles in organic synthesis. They are formed by reacting magnesium with an alkyl or aryl halide and can react with carbonyl compounds to form alcohols. In the synthesis of 3-methyl-1-phenyl-3-pentanol, a Grignard reagent derived from a two-carbon halide can be used to add a carbon chain to a carbonyl compound, facilitating the formation of the target alcohol.
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Carbonyl Chemistry
Carbonyl chemistry involves the study of compounds containing a carbonyl group (C=O), which is a key functional group in organic molecules. In the preparation of 3-methyl-1-phenyl-3-pentanol, carbonyl compounds such as ketones or aldehydes can be utilized as intermediates. The reaction of a Grignard reagent with a carbonyl compound leads to the formation of an alcohol, which is essential for achieving the final product.
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Related Practice
Textbook Question
Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.
a. How can tyramine be prepared from b-phenylethylamine?
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Textbook Question
Propose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product:
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Textbook Question
a. Explain why the following reaction leads to the products shown:
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Textbook Question
How can you distinguish the following compounds using: a. their infrared spectra?
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Textbook Question
Propose a mechanism for each of the following reactions:
b.
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