Textbook Question
Predict the major products of the following reactions, including stereochemistry.
e. trans-pent-2-ene + OsO4/H2O2
5
views
Ch.8 - Reactions of Alkenes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 34a,b
Predict the major products of the following reactions, including stereochemistry.
a. cyclohexene + KMnO4/H2O (cold, dilute)
b. cyclohexene + peroxyacetic acid in water
Verified step by step guidance1
Step 1: For reaction (a), recognize that cyclohexene reacts with cold, dilute KMnO4 in water to undergo syn-dihydroxylation. This reaction adds two hydroxyl (-OH) groups across the double bond of the cyclohexene in a syn (same side) fashion.
Step 2: Draw the structure of cyclohexene and identify the double bond. The double bond will be the site of the reaction where the hydroxyl groups are added.
Step 3: Add two hydroxyl groups (-OH) to the carbons of the double bond in a syn fashion. This means both hydroxyl groups will be on the same face of the cyclohexane ring, resulting in a cis-1,2-diol as the product.
Step 4: For reaction (b), recognize that cyclohexene reacts with peroxyacetic acid in water to form an epoxide. This reaction is known as epoxidation, where the double bond reacts with the peroxyacid to form a three-membered cyclic ether (epoxide).
Step 5: Draw the structure of cyclohexene and identify the double bond. Replace the double bond with an epoxide ring (a three-membered oxygen-containing ring). Ensure to consider stereochemistry, as the epoxide will form on one face of the cyclohexane ring.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
11mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Reactions
Oxidation reactions involve the addition of oxygen or the removal of hydrogen from a molecule. In the context of cyclohexene reacting with KMnO4, this reaction leads to the formation of diols through syn-dihydroxylation, where hydroxyl groups are added to adjacent carbon atoms in a cyclic manner, preserving stereochemistry.
Recommended video:
Guided course
03:20
Benzylic Oxidation
Stereochemistry
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving alkenes like cyclohexene, the stereochemical outcome is crucial, especially in syn-addition reactions, where the orientation of substituents on the resulting product can lead to different isomers.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Peracid Reactions
Peracid reactions involve the use of peracids, such as peroxyacetic acid, to oxidize alkenes. This reaction typically results in the formation of epoxides or diols, depending on the conditions. The mechanism involves the electrophilic attack of the peracid on the double bond, leading to the formation of a cyclic ether (epoxide) that can further react with water to yield diols.
Recommended video:
Guided course
05:09Heck Reaction
Related Practice
Textbook Question
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
3
views
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.
2
views
Textbook Question
Predict the major products of the following reactions.
b. trans-hex-3-ene + peroxyacetic acid (CH3CO3H) in water
c. 1-methylcyclohexene + MMPP in ethanol
6
views
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
Predict the major products of the following reactions, including stereochemistry.
f. trans-pent-2-ene + peroxyacetic acid in water
1
views