Textbook Question
Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene were to react with hydroxide ion. Why doesn't the reaction occur?
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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 37
Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.
Verified step by step guidance1
Step 1: Identify the reactants and products. The reactants are a carboxylic acid and diazomethane (CH₂N₂). The product is a methyl ester, along with nitrogen gas (N₂) as a byproduct.
Step 2: Recognize the role of diazomethane. Diazomethane is a highly reactive compound that acts as a methylating agent. It donates a methyl group to the carboxylic acid, converting it into a methyl ester.
Step 3: Initiate the mechanism. The carboxylic acid's hydroxyl group (-OH) acts as a nucleophile and attacks the electrophilic carbon in diazomethane. This leads to the formation of a tetrahedral intermediate.
Step 4: Rearrange the intermediate. The intermediate undergoes a rearrangement where the nitrogen atoms in diazomethane are expelled as nitrogen gas (N₂), leaving behind the methyl group attached to the oxygen atom of the carboxylic acid.
Step 5: Finalize the product. The methyl group is now bonded to the oxygen atom of the carboxylic acid, forming the methyl ester. The reaction is complete, and nitrogen gas is released as a byproduct.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are known for their acidic properties due to the ability to donate a proton (H+) from the hydroxyl part of the carboxyl group. In the context of the reaction with diazomethane, the carboxylic acid acts as the starting material that will be converted into an ester.
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Carboxylic Acids Nomenclature
Diazomethane
Diazomethane (CH2N2) is a highly reactive compound used in organic synthesis, particularly for methylation reactions. It contains a diazo group, which makes it a good methylating agent. In the proposed reaction, diazomethane reacts with the carboxylic acid to form a methyl ester, releasing nitrogen gas (N2) as a byproduct.
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03:01Reaction with diazomethane and light or heat.
Esterification Mechanism
The esterification mechanism involves the nucleophilic attack of the diazomethane on the carbonyl carbon of the carboxylic acid. This process typically includes the formation of a tetrahedral intermediate, followed by the elimination of water and the formation of the ester bond. Understanding this mechanism is crucial for proposing a detailed reaction pathway for the conversion of carboxylic acids to esters using diazomethane.
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Related Practice
Textbook Question
Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.
b. methyl orange
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Textbook Question
In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?
Textbook Question
b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.
chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene
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Textbook Question
Rank the following compounds from greatest tendency to least tendency to undergo nucleophilic aromatic substitution:
chlorobenzene
1-chloro-2,4-dinitrobenzene
p-chloronitrobenzene
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Textbook Question
Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?
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