Textbook Question
The intermediates for the oxidation of isopropanol to acetone are shown. Calculate oxidation numbers for the indicated atoms, then use them to determine in which step oxidation occurs.
(e)
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 55
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 55Chapter 12, Problem 55
Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?
Verified step by step guidance1
Understand the structure of ketones: Ketones have a carbonyl group (C=O) bonded to two carbon atoms. This makes them less reactive towards oxidation compared to aldehydes, which have a carbonyl group bonded to at least one hydrogen atom.
Examine the hydration equilibrium: The image shows a ketone in equilibrium with its hydrated form, a geminal diol. This equilibrium involves the addition of water across the carbonyl group, forming two hydroxyl groups on the same carbon.
Consider oxidation of ketones: For oxidation to occur, there must be a hydrogen atom on the carbonyl carbon that can be removed. In ketones, both groups attached to the carbonyl carbon are carbon groups, lacking the necessary hydrogen for further oxidation.
Compare with aldehydes: Aldehydes can be oxidized to carboxylic acids because they have a hydrogen atom on the carbonyl carbon, which can be replaced by an oxygen atom during oxidation.
Conclude why ketones cannot be further oxidized: Since ketones lack the hydrogen atom on the carbonyl carbon, they cannot undergo further oxidation to form carboxylic acids or other oxidized products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ketones and Aldehydes
Ketones and aldehydes are both carbonyl compounds characterized by a carbon atom double-bonded to an oxygen atom. Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, while ketones have two carbon groups attached. This structural difference influences their reactivity and stability, particularly in oxidation reactions.
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Hydration Equilibrium
Ketones and aldehydes can undergo hydration, forming their corresponding hydrate forms, which are typically more stable in aqueous solutions. This equilibrium between the carbonyl compound and its hydrate is crucial for understanding their behavior in solution, as it affects their reactivity and the extent to which they can participate in further chemical reactions.
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Oxidation of Carbonyl Compounds
Oxidation refers to the process of increasing the oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. Ketones cannot be oxidized further because they already possess the highest oxidation state for a carbonyl group, while aldehydes can be oxidized to carboxylic acids. This limitation is due to the structural stability of ketones, which prevents further oxidation under typical conditions.
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Related Practice
Textbook Question
Tertiary (3°)alcohols are not oxidized by chromic acid. Why?
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Textbook Question
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.
(a)
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Textbook Question
If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?
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Textbook Question
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.
(b)
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Textbook Question
Predict the product of the oxidation reactions shown.
(b)
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