Textbook Question
Propose a mechanism for reaction of the first three propylene units in the polymerization of propylene in the presence of a peroxide.
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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 70b
Predict the product of formula C7H13BrO from the reaction of this same unsaturated alcohol with bromine. Propose a mechanism to support your prediction.
Verified step by step guidance1
Step 1: Analyze the structure of the given unsaturated alcohol. The molecule contains a double bond (C=C) and a hydroxyl group (-OH). The double bond is the reactive site for bromine addition.
Step 2: Recall the reaction mechanism for bromine addition to alkenes. Bromine (Br2) reacts with the double bond via an electrophilic addition mechanism. The π-electrons of the double bond attack the bromine molecule, forming a bromonium ion intermediate.
Step 3: Propose the mechanism. The bromine molecule approaches the double bond, and one bromine atom becomes electrophilic. The π-electrons of the double bond attack this bromine atom, leading to the formation of a cyclic bromonium ion intermediate.
Step 4: Explain the nucleophilic attack. The second bromine atom (Br⁻) acts as a nucleophile and attacks the more substituted carbon of the bromonium ion, leading to the anti-addition of bromine across the double bond.
Step 5: Predict the product. The final product will be a dibromo compound with the bromine atoms added anti to each other across the double bond. The hydroxyl group (-OH) remains unchanged in the molecule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Unsaturated Alcohols
Unsaturated alcohols contain one or more carbon-carbon double bonds (alkenes) along with a hydroxyl (-OH) group. The presence of the double bond makes them reactive, particularly in electrophilic addition reactions. Understanding the structure and reactivity of unsaturated alcohols is crucial for predicting the products of their reactions, such as with bromine.
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02:39
The difference between saturated and unsaturated molecules.
Electrophilic Addition Mechanism
The electrophilic addition mechanism involves the reaction of an electrophile with a nucleophile, leading to the formation of a more saturated product. In the case of bromine reacting with an unsaturated alcohol, the double bond acts as a nucleophile, attacking the bromine molecule, which results in the formation of a bromonium ion intermediate. This step is essential for understanding how the final product is formed.
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05:39Features of Addition Mechanisms.
Halohydrin Formation
Halohydrin formation occurs when an alkene reacts with a halogen (like bromine) in the presence of water or an alcohol, resulting in the addition of both a halogen and a hydroxyl group across the double bond. This reaction typically proceeds through a bromonium ion intermediate, leading to the formation of a product that contains both a halogen and an alcohol functional group, which is relevant for predicting the product of the given reaction.
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01:44General properties of halohydrin formation.
Related Practice
Textbook Question
When styrene (vinylbenzene) is commercially polymerized, about 1–3% of 1,4-divinylbenzene is often added to the styrene. The incorporation of some divinylbenzene gives a polymer with more strength and better resistance to organic solvents. Explain how a very small amount of divinylbenzene has a marked effect on the properties of the polymer.
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Textbook Question
An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic reduction to give decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-cyclohexane-1,2-dicarboxylic acid and oxalic acid. Propose a structure for the unknown compound.
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Textbook Question
The following cyclization has been observed in the oxymercuration-demercuration of this unsaturated alcohol. Propose a mechanism for this reaction.
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Textbook Question
The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.
Show how you would convert
c. maleic acid to (±)-tartaric acid.
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Textbook Question
A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.
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