Textbook Question
Predict the major products of the following reactions, including stereochemistry.
a. cyclohexene + KMnO4/H2O (cold, dilute)
b. cyclohexene + peroxyacetic acid in water
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Ch.8 - Reactions of Alkenes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 8, Problem 34c,d
Predict the major products of the following reactions, including stereochemistry.
c. cis-pent-2-ene + OsO4/H2O2
d. cis-pent-2-ene + peroxyacetic acid in water
Verified step by step guidance1
Step 1: Analyze the reaction conditions for part (c). The reagents OsO4 (osmium tetroxide) and H2O2 (hydrogen peroxide) are used for dihydroxylation. This reaction adds two hydroxyl (-OH) groups to the double bond of the alkene in a syn addition manner, meaning both hydroxyl groups will be added to the same face of the molecule.
Step 2: Identify the structure of cis-pent-2-ene. It is an alkene with a double bond between the second and third carbons, and the substituents on the double bond are on the same side (cis configuration). This stereochemistry will influence the product.
Step 3: Predict the product for part (c). The syn addition of two hydroxyl groups will occur across the double bond, resulting in a diol (a molecule with two hydroxyl groups). The stereochemistry of the product will reflect the cis configuration of the starting alkene, meaning the hydroxyl groups will be added to the same side of the molecule.
Step 4: Analyze the reaction conditions for part (d). The reagents peroxyacetic acid in water indicate an epoxidation reaction followed by hydrolysis. Peroxyacetic acid will convert the double bond of cis-pent-2-ene into an epoxide (a three-membered cyclic ether). In the presence of water, the epoxide will undergo hydrolysis to form a diol.
Step 5: Predict the product for part (d). The hydrolysis of the epoxide will result in the addition of two hydroxyl groups to the double bond. Since the starting alkene is cis-pent-2-ene, the stereochemistry of the product will reflect the cis configuration, but the hydroxyl groups will be added in an anti fashion due to the mechanism of epoxide opening.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In organic reactions, stereochemistry is crucial for predicting the configuration of products, especially in reactions involving alkenes, where the orientation of substituents can lead to different stereoisomers.
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Dihydroxylation
Dihydroxylation is a chemical reaction that involves the addition of two hydroxyl (–OH) groups across a double bond in alkenes. This reaction can occur via syn or anti addition, and the choice of reagent, such as OsO4 or peroxyacetic acid, influences the stereochemical outcome of the product.
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03:50General properties of syn vicinal dihydroxylation.
Oxidation Reagents
Oxidation reagents like OsO4 and peroxyacetic acid are used to convert alkenes into diols through different mechanisms. OsO4 typically leads to syn-dihydroxylation, while peroxyacetic acid can also facilitate the formation of diols but may involve different pathways, affecting the stereochemistry of the final products.
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Related Practice
Textbook Question
Predict the major products of the following reactions, including stereochemistry.
e. trans-pent-2-ene + OsO4/H2O2
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Textbook Question
When 1,2-epoxycyclohexane (cyclohexene oxide) is treated with anhydrous HCl in methanol, the principal product is trans-2-methoxycyclohexanol. Propose a mechanism to account for the formation of this product.
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Textbook Question
Predict the major products of the following reactions.
d. trans-cyclodecene + peroxyacetic acid in acidic water
e. cis-cyclodecene + mCPBA in CH2Cl2, then dilute aqueous acid
Textbook Question
Show how you would accomplish the following conversions.
a. cis-hex-3-ene to meso-hexane-3,4-diol
Textbook Question
Predict the major products of the following reactions, including stereochemistry.
f. trans-pent-2-ene + peroxyacetic acid in water
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