Textbook Question
Draw the products of the following reactions:
a.
3
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Ch. 17 - Reactions at the Alpha-Carbon
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 18, Problem 53d
Draw the products of the following reactions:
d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCl
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a Claisen condensation reaction, where diethyl 1,2-benzenedicarboxylate (an ester) reacts with ethyl acetate (another ester) in the presence of a strong base (sodium ethoxide). The reaction involves the formation of a β-keto ester intermediate.
Step 2: Deprotonation of the α-hydrogen. Sodium ethoxide (NaOEt) acts as a base and deprotonates the α-hydrogen of ethyl acetate, forming an enolate ion. The enolate ion is a nucleophile that will attack the electrophilic carbonyl carbon of the diethyl 1,2-benzenedicarboxylate.
Step 3: Nucleophilic attack. The enolate ion attacks one of the ester carbonyl carbons in diethyl 1,2-benzenedicarboxylate, leading to the formation of a tetrahedral intermediate. This intermediate then collapses, expelling an ethoxide ion (EtO⁻) as a leaving group and forming a β-keto ester.
Step 4: Acidic workup. After the slow addition of ethyl acetate and completion of the reaction, the mixture is treated with HCl. The acidic workup neutralizes the base and stabilizes the β-keto ester product.
Step 5: Draw the product. The final product is a β-keto ester where the ethyl acetate has been added to the diethyl 1,2-benzenedicarboxylate framework. Ensure to include the aromatic ring and the ester groups in the structure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Esterification Reaction
Esterification is a chemical reaction that forms an ester from an alcohol and a carboxylic acid. In this context, diethyl 1,2-benzenedicarboxylate reacts with sodium ethoxide, which acts as a base, facilitating the nucleophilic attack of ethyl acetate on the carbonyl carbon of the ester. This reaction is crucial for understanding how the products are formed in the given reaction sequence.
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Reactions of Amino Acids: Esterification Concept 1
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, the ethoxide ion acts as a nucleophile, attacking the electrophilic carbon of the diethyl 1,2-benzenedicarboxylate. Understanding this mechanism is essential for predicting the products of the reaction after the slow addition of ethyl acetate.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Acid-Base Reaction
An acid-base reaction involves the transfer of protons (H+) between reactants. After the nucleophilic substitution, the addition of HCl serves to protonate the alkoxide ion formed, converting it back to an alcohol. This step is important for completing the reaction and understanding the final products, as it influences the stability and reactivity of the intermediates.
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02:49The Lewis definition of acids and bases.
Related Practice
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Draw the products of the following reactions:
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