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What are the products of the following reactions?
i.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 66j
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 66jCapitolo 16, Problema 66j
What are the products of the following reactions?
j. 
Guida verificata passo dopo passo1
Step 1: Identify the reactants. Ethyl acrylate is an ester with an α,β-unsaturated carbonyl group, and ethanamine is a primary amine. This reaction involves nucleophilic addition or substitution.
Step 2: Recognize the reactivity of the α,β-unsaturated carbonyl group in ethyl acrylate. The double bond adjacent to the carbonyl group is electrophilic due to resonance stabilization, making it susceptible to nucleophilic attack.
Step 3: Ethanamine, as a nucleophile, will attack the electrophilic β-carbon of the α,β-unsaturated system in ethyl acrylate. This is a typical Michael addition reaction mechanism.
Step 4: After the nucleophilic attack, the intermediate formed undergoes proton transfer to stabilize the molecule. This results in the formation of a new bond between the amine and the β-carbon of ethyl acrylate.
Step 5: The final product is a β-amino ester, where the ethyl acrylate has been modified by the addition of ethanamine at the β-carbon position.
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Conjugate Addition
Conjugate addition refers to the reaction where a nucleophile adds to the β-carbon of an α,β-unsaturated carbonyl compound. This process typically involves the attack of a nucleophile, such as an amine, on the double bond adjacent to the carbonyl group, leading to the formation of a new bond and a product that retains the carbonyl functionality.
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Reactivity of α,β-Unsaturated Carbonyl Compounds
α,β-Unsaturated carbonyl compounds, like ethyl acrylate, are highly reactive due to the presence of both a double bond and a carbonyl group. The electron-withdrawing nature of the carbonyl enhances the electrophilicity of the β-carbon, making it susceptible to nucleophilic attack, which is a key feature in many organic reactions, including conjugate additions.
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Nucleophiles in Organic Reactions
Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In this context, ethanamine acts as a nucleophile, attacking the electrophilic β-carbon of ethyl acrylate. Understanding the nature of nucleophiles and their reactivity is crucial for predicting the products of organic reactions, particularly in conjugate addition scenarios.
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