Textbook Question
Show each step in the mechanism of the acid-catalyzed interconversion of (R)- and (S)-3-methylpentan-2-one.
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Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
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Wade 9th EditionCh. 22 - Condensations and Alpha Substitutions of Carbonyl CompoundsProblem 1c4
Wade 9th EditionCh. 22 - Condensations and Alpha Substitutions of Carbonyl CompoundsProblem 1c4Chapter 22, Problem 1c4
Phenylacetone can form two different enols.
(c) Propose mechanisms for the formation of the second enol in base.
Verified step by step guidance1
Identify the structure of phenylacetone: It consists of a phenyl group (C₆H₅-) attached to a carbonyl group (C=O) via a CH₂ group. The molecule is CH₃-CO-CH₂-C₆H₅.
Understand enol formation: Enols are formed by the tautomerization of ketones or aldehydes. In the presence of a base, the alpha-hydrogen (hydrogen on the carbon adjacent to the carbonyl group) is abstracted, leading to the formation of an enolate ion, which can then tautomerize to form the enol.
Propose the mechanism for the second enol formation: (1) A base (e.g., OH⁻) abstracts the alpha-hydrogen from the CH₃ group adjacent to the carbonyl group, forming an enolate ion. (2) The negative charge on the enolate ion delocalizes between the alpha-carbon and the oxygen atom of the carbonyl group, creating resonance structures.
Explain the tautomerization step: The enolate ion undergoes protonation at the oxygen atom, leading to the formation of the enol. The second enol is formed when the double bond is between the alpha-carbon and the carbonyl carbon, and the hydroxyl group (-OH) is attached to the carbonyl carbon.
Summarize the key points: The second enol is formed through base-catalyzed deprotonation of the alpha-hydrogen, resonance stabilization of the enolate ion, and subsequent protonation to yield the enol with a different double bond and hydroxyl group arrangement compared to the first enol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Enol Formation
Enol formation involves the conversion of a carbonyl compound, such as a ketone or aldehyde, into its corresponding enol form, which features a double bond between a carbon and an adjacent carbon with a hydroxyl group. This process is often facilitated by acid or base catalysis, where the base abstracts a proton from the alpha carbon, leading to the formation of a resonance-stabilized enolate ion that can then re-protonate to form the enol.
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Formation of Enolates
Base Catalysis
Base catalysis refers to the use of a base to facilitate a chemical reaction. In the context of enol formation, a base can deprotonate the alpha carbon of a carbonyl compound, generating an enolate ion. This ion is more nucleophilic and can participate in further reactions, such as nucleophilic addition or rearrangement, ultimately leading to the formation of different enol isomers.
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Tautomerization
Tautomerization is a chemical equilibrium between two isomers, typically involving the migration of a hydrogen atom and a switch of a double bond. In the case of phenylacetone, the keto form can tautomerize to the enol form, and this process can yield different enol structures depending on the reaction conditions. Understanding tautomerization is crucial for predicting the products of reactions involving carbonyl compounds.
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Related Practice
Textbook Question
Phenylacetone can form two different enols.
(c) Propose mechanisms for the formation of the first enol in base.
731
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Textbook Question
Phenylacetone can form two different enols.
(c) Propose mechanisms for the formation of the second enol in acid.
567
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Textbook Question
Phenylacetone can form two different enols.
(a) Show the structures of these enols.
(b) Predict which enol will be present in the larger concentration at equilibrium.
940
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Textbook Question
Phenylacetone can form two different enols.
(c) Propose mechanisms for the formation of the first enol in acid.
887
views