Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
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Ch. 11 - Organometallic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 12, Problem 49a
What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)
a. 
Verified step by step guidance1
Step 1: Identify the compound provided in the image. The structure is a bicyclic compound containing a strained cyclobutene ring fused to a cyclohexene ring. The double bond in the cyclohexene ring is the reactive site for ring-opening metathesis polymerization (ROMP).
Step 2: Understand the mechanism of ring-opening metathesis polymerization (ROMP). ROMP involves the cleavage of a strained cyclic alkene, followed by polymerization through a metathesis reaction. The driving force is the release of ring strain, leading to the formation of a linear polymer.
Step 3: Predict the product of ROMP. The polymerization will result in a high molecular weight unsaturated hydrocarbon. The repeating unit in the polymer corresponds to the structure of the monomer after the ring has opened. The double bond in the monomer will remain in the polymer chain, contributing to unsaturation.
Step 4: Analyze the structure after ring opening. The cyclobutene ring opens to form a linear chain, while the cyclohexene ring contributes to the repeating unit. The polymer will consist of alternating double bonds along the backbone, maintaining the unsaturation characteristic.
Step 5: Conclude the product. The product is a linear unsaturated hydrocarbon polymer with repeating units derived from the monomer. The polymer backbone will contain alternating double bonds, resulting in a conjugated system with high molecular weight.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ring-Opening Metathesis Polymerization (ROMP)
ROMP is a type of polymerization that involves the opening of a cyclic compound to form a polymer. This process typically utilizes transition metal catalysts to facilitate the reaction, allowing for the formation of unsaturated polymers. The reaction is characterized by the exchange of alkene groups, leading to the creation of long-chain hydrocarbons with high molecular weights.
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Acid-Catalyzed Epoxide Ring-Opening
Unsaturated Hydrocarbons
Unsaturated hydrocarbons are organic compounds that contain at least one double or triple bond between carbon atoms. These compounds are significant in organic chemistry as they can undergo various reactions, including polymerization. The presence of double bonds in the product of ROMP contributes to the reactivity and properties of the resulting polymer, making it useful in various applications.
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02:39The difference between saturated and unsaturated molecules.
Molecular Weight in Polymers
Molecular weight refers to the mass of a molecule, and in the context of polymers, it indicates the size of the polymer chains formed during polymerization. High molecular weight polymers typically exhibit enhanced mechanical properties and stability. Understanding the relationship between the starting monomer and the resulting polymer's molecular weight is crucial for predicting the material's behavior and applications.
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1:49Introduction to Polymers Concept 1
Related Practice
Textbook Question
Metathesis of which of the following sets of alkenes leads to the highest yield of a single alkene?
1. 1-butene and 1-pentene
2. 2-butene and 3-hexene
3. 2-butene and 1-pentene
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Textbook Question
The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur.
The organozinc reagent is prepared by treating an α-bromo ester with zinc.
Describe how each of the following compounds can be prepared, using a Reformatsky reaction:
d.
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Textbook Question
A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C6H5-CH3) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.
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Textbook Question
What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?
a.
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Textbook Question
What are the products of the following reactions? Show all stereoisomers that are formed.
a.
b.
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