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 22d
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) 
Verified step by step guidance1
Step 1: Understand the permanganate test. The permanganate test is used to identify the presence of unsaturated compounds, such as alkenes or alkynes, or functional groups that can be oxidized, such as alcohols or aldehydes. A positive test results in the purple KMnO₄ solution turning brown due to the formation of MnO₂.
Step 2: Analyze the structure of the molecule provided. The molecule contains a hydroxyl group (-OH) attached to a carbon adjacent to a ketone group (C=O). This is a beta-hydroxy ketone structure.
Step 3: Determine if the functional groups present can be oxidized by KMnO₄. The hydroxyl group (-OH) is capable of being oxidized by KMnO₄ under appropriate conditions, which could lead to a positive permanganate test.
Step 4: Consider the cyclic structure. The cyclohexane ring in the molecule is saturated and does not contain double or triple bonds, so it will not react with KMnO₄. The reactivity is focused on the hydroxyl group.
Step 5: Conclude that the molecule is likely to give a positive permanganate test due to the presence of the oxidizable hydroxyl group (-OH). The purple KMnO₄ solution would turn brown as the hydroxyl group is oxidized.
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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 certain other functional groups in organic compounds. When an alkene is present, the purple color of potassium permanganate (KMnO₄) is reduced to brown manganese dioxide (MnO₂), indicating a reaction. This test is particularly useful for identifying unsaturation in organic molecules.
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Oxidation of Alcohols
Alcohols can undergo oxidation reactions, where they are converted into carbonyl compounds such as aldehydes or ketones. The permanganate test can also indicate the presence of primary and secondary alcohols, as they can be oxidized to aldehydes and ketones, respectively. Tertiary alcohols, however, do not react in this manner, making this concept crucial for interpreting the test results.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the permanganate test, the presence of double bonds (alkenes) or hydroxyl groups (alcohols) can significantly influence the outcome of the test. Understanding the functional groups present in the molecules A-D is essential for predicting their reactivity with KMnO₄.
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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?
(c)
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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
Show an arrow-pushing mechanism for reactions 1–4 in Figure 9.37.
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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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