Textbook Question
Provide a mechanism for the formation of the hemiacetals shown. [Only (c) is favored as written.]
(a)
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Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones
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. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 54
Mullins 1st EditionCh. 17 - Carbonyl Addition Reactions: Aldehydes and KetonesProblem 54Chapter 16, Problem 54
During an oxidation reaction, there must also be a reduction. What is reduced in the Pinnick oxidation?
Verified step by step guidance1
Understand the Pinnick oxidation: It is a chemical reaction used to oxidize aldehydes to carboxylic acids using sodium chlorite (NaClO2) as the oxidizing agent.
Identify the role of sodium chlorite (NaClO2): In the Pinnick oxidation, sodium chlorite acts as the oxidizing agent, meaning it will be reduced during the reaction.
Recognize the concept of redox reactions: In any redox reaction, oxidation and reduction occur simultaneously. The substance that is oxidized loses electrons, while the substance that is reduced gains electrons.
Determine what is reduced: In the Pinnick oxidation, sodium chlorite (NaClO2) is reduced to chloride ions (Cl-) as it oxidizes the aldehyde to a carboxylic acid.
Summarize the redox process: The aldehyde is oxidized to a carboxylic acid, and sodium chlorite is reduced to chloride ions, completing the redox cycle in the Pinnick oxidation.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation-Reduction Reactions
Oxidation-reduction (redox) reactions involve the transfer of electrons between two species. Oxidation refers to the loss of electrons, while reduction refers to the gain of electrons. In any redox reaction, one species is oxidized and another is reduced, maintaining the balance of electron transfer.
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Distinguishing between Oxidation and Reduction
Pinnick Oxidation
Pinnick oxidation is a chemical reaction used to convert aldehydes into carboxylic acids using sodium chlorite (NaClO2) as the oxidizing agent. This reaction is often performed in the presence of a buffer to maintain a neutral pH, which helps in the selective oxidation of aldehydes without affecting other functional groups.
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Role of Sodium Chlorite
In the Pinnick oxidation, sodium chlorite (NaClO2) acts as the oxidizing agent. During the reaction, sodium chlorite is reduced to chloride ions (Cl-) while oxidizing the aldehyde to a carboxylic acid. This reduction of sodium chlorite is essential for the overall redox balance of the reaction.
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Related Practice
Textbook Question
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
b. (R)-6-bromo-7-oxoheptan-2-one
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Textbook Question
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
d. (E)-2-methylhex-2-en-6-al
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Textbook Question
Show the product expected by the Wolff–Kishner reduction of the following aldehydes/ketones.
(a)
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Textbook Question
The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.
(a) 3-oxo-5-methylhexan-2-ol
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Textbook Question
Which of the following cyclic hemiacetals would you expect to have the highest Keq for their formation? Explain your answer.
(a)
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