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.
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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 54
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 54Chapter 12, Problem 54
Tertiary (3°)alcohols are not oxidized by chromic acid. Why?
Verified step by step guidance1
Understand the structure of tertiary alcohols: Tertiary alcohols have the hydroxyl group (-OH) attached to a carbon atom that is connected to three other carbon atoms. This means there are no hydrogen atoms directly attached to the carbon bearing the hydroxyl group.
Review the oxidation process: Oxidation of alcohols typically involves the removal of hydrogen atoms from the carbon atom bonded to the hydroxyl group, forming a carbonyl group. For primary and secondary alcohols, this process is possible because they have hydrogen atoms attached to the carbon with the hydroxyl group.
Consider the role of chromic acid: Chromic acid (H₂CrO₄) is a strong oxidizing agent that can convert primary alcohols to carboxylic acids and secondary alcohols to ketones by removing hydrogen atoms from the carbon atom bonded to the hydroxyl group.
Analyze the limitation with tertiary alcohols: Since tertiary alcohols lack hydrogen atoms on the carbon with the hydroxyl group, chromic acid cannot facilitate the removal of hydrogen atoms to form a carbonyl group. Therefore, tertiary alcohols cannot be oxidized by chromic acid.
Conclude the reasoning: The absence of hydrogen atoms on the carbon atom bonded to the hydroxyl group in tertiary alcohols prevents the oxidation process, making them resistant to oxidation by chromic acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Alcohols
Oxidation in organic chemistry refers to the process where a molecule loses electrons, often involving the addition of oxygen or removal of hydrogen. Primary and secondary alcohols can be oxidized to aldehydes and ketones, respectively, using oxidizing agents like chromic acid. However, tertiary alcohols lack a hydrogen atom on the carbon bearing the hydroxyl group, making them resistant to oxidation.
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Structure of Tertiary Alcohols
Tertiary alcohols have the hydroxyl group (-OH) attached to a carbon atom that is connected to three other carbon atoms. This structure means there is no hydrogen atom on the carbon with the hydroxyl group, which is necessary for oxidation to occur. Without this hydrogen, the typical oxidation pathway cannot proceed, preventing the formation of carbonyl compounds.
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Chromic Acid as an Oxidizing Agent
Chromic acid (H2CrO4) is a strong oxidizing agent commonly used to oxidize primary and secondary alcohols to aldehydes and ketones. It works by accepting electrons from the alcohol, facilitating the removal of hydrogen atoms. However, in tertiary alcohols, the absence of a hydrogen atom on the hydroxyl-bearing carbon means chromic acid cannot initiate the oxidation process, leaving the alcohol unchanged.
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Related Practice
Textbook Question
Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.
(a)
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Textbook Question
Predict the product of the oxidation reactions shown.
(a)
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
Predict the product of the oxidation reactions shown.
(b)
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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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