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 56
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 56Chapter 12, Problem 56
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?
Verified step by step guidance1
Understand the structure of an aldehyde: An aldehyde has the general formula RCHO, where R is a hydrocarbon group and CHO is the aldehyde functional group.
Recognize the oxidation process: Oxidation in organic chemistry typically involves the increase in the number of bonds to oxygen or the decrease in the number of bonds to hydrogen.
Identify the oxidizing agent: Common oxidizing agents for aldehydes include potassium permanganate (KMnO4), chromic acid (H2CrO4), and silver oxide (Ag2O). These agents can facilitate the conversion of an aldehyde to a carboxylic acid.
Consider the reaction mechanism: The oxidation of an aldehyde to a carboxylic acid involves the addition of an oxygen atom to the carbonyl carbon, increasing its oxidation state.
Conclude the possibility: Yes, an aldehyde can be oxidized to a carboxylic acid even without forming a hydrate, as the oxidation process directly involves the aldehyde functional group and an oxidizing agent.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aldehyde Structure and Reactivity
Aldehydes are organic compounds characterized by the presence of a carbonyl group (C=O) bonded to a hydrogen atom and an R group. This structure makes them susceptible to oxidation, where the hydrogen atom is replaced by a hydroxyl group, forming a carboxylic acid. Understanding the reactivity of the carbonyl group is crucial for predicting oxidation reactions.
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Oxidation of Aldehydes
Oxidation is a chemical reaction involving the loss of electrons. Aldehydes can be oxidized to carboxylic acids by various oxidizing agents, such as potassium permanganate (KMnO4) or chromic acid (H2CrO4). This process involves the conversion of the aldehyde's hydrogen atom into a hydroxyl group, increasing the oxidation state of the carbon atom.
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Role of Water in Hydrate Formation
Hydrate formation involves the addition of water to an aldehyde, resulting in a geminal diol. This reaction is reversible and depends on the presence of water. While hydrates are intermediates in some oxidation reactions, the absence of water prevents their formation, but does not impede the direct oxidation of aldehydes to carboxylic acids.
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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.
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Textbook Question
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.
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Textbook Question
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.
(c)
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Textbook Question
Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?
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