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 95
Propose a mechanism for each of the following reactions:
b. 
Verified step by step guidance1
Step 1: Analyze the reactants and products. The starting material contains a hydroxyl group (-OH) and a sulfone group (-SO2) attached to a benzene ring. The product shows the formation of an ether bond (-O-) between two aromatic rings, with the sulfone group now bearing a negative charge.
Step 2: Recognize the role of the reagent, NaOCH3. Sodium methoxide (NaOCH3) is a strong base and can deprotonate the hydroxyl group (-OH) on the benzene ring, forming a phenoxide ion (-O⁻). This phenoxide ion is highly nucleophilic.
Step 3: Propose the nucleophilic attack mechanism. The phenoxide ion generated in Step 2 can attack the electrophilic sulfone group (-SO2) on the adjacent benzene ring. This results in the formation of a new ether bond (-O-) between the two aromatic rings.
Step 4: Account for the charge distribution. After the nucleophilic attack, the sulfone group (-SO2) loses one of its oxygen atoms to form a negatively charged sulfonate group (-SO2⁻). This charge is stabilized by resonance within the sulfonate group.
Step 5: Verify the mechanism consistency. Ensure that the proposed mechanism aligns with the observed product structure, including the ether bond formation and the sulfonate group (-SO2⁻) in the final product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Williamson Ether Synthesis
Williamson Ether Synthesis is a method for producing ethers through the reaction of an alkoxide ion with a primary alkyl halide. In this reaction, the alkoxide acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide, leading to the formation of an ether. This reaction is particularly effective with primary halides to avoid elimination reactions.
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The Mechanism of Williamson Ether Synthesis.
Nucleophilic Substitution Mechanism
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. This can occur via two main pathways: SN1, which involves a two-step mechanism with a carbocation intermediate, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. The choice of mechanism depends on the structure of the substrate and the conditions of the reaction.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Alkoxide Ion
An alkoxide ion is a deprotonated alcohol, represented as R-O⁻, where R is an alkyl group. Alkoxides are strong nucleophiles and are commonly used in organic synthesis, particularly in reactions like Williamson Ether Synthesis. They can be generated by treating alcohols with strong bases, such as sodium hydride or sodium metal, making them highly reactive in forming new carbon-oxygen bonds.
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Related Practice
Textbook Question
Show how the following compounds can be prepared from benzene:
c.
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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
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.
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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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