Textbook Question
There are two mechanisms by which each of the two enantiomers can form in the reaction shown in Figure 9.37. Show them.
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Ch. 9 - Alkenes II: Oxidation and Reduction
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
Chapter 8, Problem 22c
Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?
(c) 
Verified step by step guidance1
Step 1: Understand the permanganate test. The permanganate test is used to identify the presence of unsaturation (double or triple bonds) or certain functional groups like alcohols or aldehydes. A positive test results in the purple KMnO₄ solution turning brown due to the formation of MnO₂.
Step 2: Analyze the given molecule. The structure provided is an ether, specifically diisopropyl ether. It contains no double or triple bonds and no functional groups like alcohols or aldehydes that can react with KMnO₄.
Step 3: Recall the reactivity of ethers. Ethers are generally inert to KMnO₄ under standard conditions because they lack the functional groups required for oxidation.
Step 4: Compare with the criteria for a positive permanganate test. Since the molecule does not have unsaturation or oxidizable functional groups, it would not give a positive permanganate test.
Step 5: Conclude that the molecule shown in the image would not result in the purple KMnO₄ solution turning brown, as it does not meet the requirements for a positive test.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Permanganate Test
The permanganate test is a qualitative analysis used to detect the presence of alkenes and alkynes in organic compounds. When these unsaturated hydrocarbons react with potassium permanganate (KMnO₄), the purple color of the solution is reduced to brown manganese dioxide (MnO₂), indicating a positive result. This reaction is due to the oxidation of the double or triple bonds present in the molecules.
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Unsaturation in Organic Molecules
Unsaturation refers to the presence of double or triple bonds between carbon atoms in organic molecules. These unsaturated bonds are reactive and can participate in addition reactions, making them susceptible to oxidation by reagents like KMnO₄. Identifying whether a molecule is saturated (single bonds only) or unsaturated is crucial for predicting its behavior in the permanganate test.
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02:39The difference between saturated and unsaturated molecules.
Oxidation-Reduction Reactions
Oxidation-reduction (redox) reactions involve the transfer of electrons between substances, leading to changes in oxidation states. In the context of the permanganate test, the unsaturated organic compound is oxidized, while the permanganate ion is reduced, resulting in the color change from purple to brown. Understanding these reactions is essential for interpreting the results of the test and determining the presence of unsaturation in the tested molecules.
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Related Practice
Textbook Question
Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?
(d)
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Textbook Question
When using a terminal alkene under the conditions shown here, explain why it is unnecessary to show the relative stereochemical outcome in the product.
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Textbook Question
Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(c)
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Textbook Question
Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(b)
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Textbook Question
The concertedness of the OsO4 reaction results in both oxygens being added to the same face of the molecule (i.e., syn addition). How might these conditions be modified in order to prepare a trans-diol?
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