Textbook Question
Predict the major products of the following reactions, including stereochemistry.
a. cyclohexene + KMnO4/H2O (cold, dilute)
b. cyclohexene + peroxyacetic acid in water
1
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 32d,e
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
Verified step by step guidance1
Step 1: Recognize that both reactions involve the epoxidation of alkenes followed by acid-catalyzed ring opening of the epoxide. The reagents used (peroxyacetic acid and mCPBA) are common peroxy acids for epoxidation.
Step 2: For reaction (d), trans-cyclodecene reacts with peroxyacetic acid (CH₃COOOH) to form a trans-epoxide. The stereochemistry of the alkene dictates the stereochemistry of the epoxide, maintaining the trans configuration.
Step 3: In the second step of reaction (d), the acidic water (H₃O⁺) opens the epoxide ring via protonation of the oxygen atom, followed by nucleophilic attack by water. This results in a diol with anti stereochemistry due to the trans configuration of the starting material.
Step 4: For reaction (e), cis-cyclodecene reacts with mCPBA in CH₂Cl₂ to form a cis-epoxide. The stereochemistry of the alkene dictates the stereochemistry of the epoxide, maintaining the cis configuration.
Step 5: In the second step of reaction (e), the acidic water (H₃O⁺) opens the epoxide ring via protonation of the oxygen atom, followed by nucleophilic attack by water. This results in a diol with syn stereochemistry due to the cis configuration of the starting material.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
10mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition Reactions
Electrophilic addition reactions involve the addition of electrophiles to nucleophilic sites in alkenes or alkynes. In the context of the reactions provided, the double bonds in trans-cyclodecene and cis-cyclodecene act as nucleophiles, reacting with electrophiles such as peroxyacetic acid and mCPBA, leading to the formation of new bonds and products.
Recommended video:
Guided course
05:39
Features of Addition Mechanisms.
Peracid Reactions
Peracids, like peroxyacetic acid and mCPBA, are strong oxidizing agents that can facilitate the formation of epoxides from alkenes. In the reactions described, these peracids react with the double bonds to form epoxide intermediates, which can then undergo further reactions in acidic conditions to yield diols or other products.
Recommended video:
Guided course
05:09Heck Reaction
Acid-Catalyzed Hydrolysis
Acid-catalyzed hydrolysis is a reaction where water, in the presence of an acid, reacts with an epoxide or other reactive intermediate to form alcohols. In the given reactions, after the formation of epoxides, the addition of dilute aqueous acid (H3O+) leads to the opening of the epoxide ring, resulting in the formation of diols as the final products.
Recommended video:
Guided course
03:09Acid Catalyzed
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
Magnesium monoperoxyphthalate (MMPP) epoxidizes alkenes much like mCPBA. MMPP is more stable, however, and it may be safer to use for large-scale and industrial reactions. Propose a mechanism for the reaction of trans-2-methylhept-3-ene with MMPP, and predict the structure of the product(s).
2
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.
a. cis-hex-2-ene + mCPBA in chloroform
3
views