Textbook Question
Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:
b.
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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 65b
There are other condensation reactions similar to the aldol and Claisen condensations:
b. What compound is formed if water is added to the product of a Perkin condensation?
Verified step by step guidance1
Step 1: Understand the Perkin condensation reaction. It involves the reaction of an aromatic aldehyde with an anhydride in the presence of a base to form an α,β-unsaturated carboxylic acid derivative.
Step 2: Analyze the product of the Perkin condensation shown in the image. The product is an α,β-unsaturated carboxylic acid derivative with a conjugated double bond system.
Step 3: Consider the addition of water to the product. Water can hydrolyze the double bond in the α,β-unsaturated system under certain conditions, leading to hydration at the β-carbon.
Step 4: The hydration reaction typically forms a β-hydroxy carboxylic acid. This occurs because water adds across the double bond, with the hydroxyl group attaching to the β-carbon and the hydrogen attaching to the α-carbon.
Step 5: The final compound formed after water addition is a β-hydroxy derivative of the original α,β-unsaturated carboxylic acid. This transformation is a key step in understanding the reactivity of α,β-unsaturated systems in organic chemistry.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Perkin Condensation
The Perkin condensation is a reaction between an aromatic aldehyde and an anhydride, typically yielding α,β-unsaturated carboxylic acids. This reaction involves the formation of a carbon-carbon bond through the nucleophilic attack of the enolate ion derived from the anhydride on the carbonyl carbon of the aldehyde, followed by dehydration to form the final product.
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Condensation Reactions
Hydrolysis
Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of the Perkin condensation product, adding water can lead to the conversion of the α,β-unsaturated carboxylic acid into its corresponding carboxylic acid and alcohol, effectively reversing the condensation process and yielding more stable products.
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Condensation Reactions
Condensation reactions are a class of reactions where two molecules combine to form a larger molecule, typically with the loss of a small molecule such as water. In organic chemistry, these reactions are crucial for forming complex structures and are foundational in synthesizing various organic compounds, including those formed in aldol and Claisen condensations, as well as the Perkin reaction.
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Related Practice
Textbook Question
There are other condensation reactions similar to the aldol and Claisen condensations:
c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no a-hydrogens and a compound such as diethyl malonate that has an a-carbon flanked by two electron-withdrawing groups. Draw the product obtained from the following Knoevenagel condensation:
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Textbook Question
There are other condensation reactions similar to the aldol and Claisen condensations:
a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation:
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Textbook Question
A β-ɣ-unsaturated carbonyl compound rearranges to a more stable conjugated ⍺,β-unsaturated compound in the presence of either acid or base. b. Propose a mechanism for the acid-catalyzed rearrangement.
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Textbook Question
Show how the following compound can be synthesized from the given starting material. (Hint: Start with an acetoacetic ester.)
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Textbook Question
What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?
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