Textbook Question
Determine whether the following reactions are redox reactions. If they are, identify whether the molecule has been oxidized or reduced.
(d)
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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 45d(vi)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO4 2. NaHSO3
(d) 
Verified step by step guidance1
Step 1: Recognize the reaction type. The reagents OsO₄ (osmium tetroxide) followed by NaHSO₃ (sodium bisulfite) indicate a dihydroxylation reaction. This reaction adds two hydroxyl (-OH) groups to the alkene in a syn addition manner.
Step 2: Identify the structure of the alkene. The double bond in the alkene is the reactive site where the addition of hydroxyl groups will occur.
Step 3: Understand the mechanism. OsO₄ reacts with the alkene to form a cyclic osmate ester intermediate. This intermediate ensures that the two hydroxyl groups are added to the same face of the double bond (syn addition).
Step 4: Use NaHSO₃ to cleave the osmate ester. Sodium bisulfite is used in the second step to hydrolyze the osmate ester, releasing the diol (a molecule with two hydroxyl groups) as the final product.
Step 5: Predict the stereochemistry of the product. Since the addition is syn, the two hydroxyl groups will be on the same side of the former double bond. If the alkene is cyclic or has substituents, consider the stereochemical implications of the syn addition.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkene Reactivity
Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various addition reactions. Understanding how alkenes react with different reagents is crucial for predicting the products of these reactions.
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Alkene Metathesis Concept 1
Osmium Tetroxide (OsO₄) Reaction
Osmium tetroxide is a powerful oxidizing agent used in organic chemistry to convert alkenes into vicinal diols (glycols) through syn-dihydroxylation. This reaction involves the addition of hydroxyl groups (–OH) across the double bond, resulting in a compound with two adjacent alcohol groups. The stereochemistry of the product is important, as it retains the configuration of the alkene.
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Sodium Bisulfite (NaHSO₃) Workup
Sodium bisulfite is often used in organic reactions as a reducing agent and for the purification of reaction products. In the context of the OsO₄ reaction, NaHSO₃ serves to quench the reaction and can help isolate the diol product by forming a stable bisulfite adduct. This step is essential for ensuring that the desired product is obtained in a pure form.
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Related Practice
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ii) Cl2
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2, Pd/C.
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl2, CH3OH
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br2, H2O
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