Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(a)
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 52c
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(c) 
Verified step by step guidance1
Step 1: Identify the reactants involved in the metathesis reaction. The first reactant is eugenol, which contains a terminal alkene group. The second reactant is a diol with a terminal alkene group. The catalyst used is either a Schrock or Grubbs catalyst, which facilitates the metathesis reaction.
Step 2: Understand the mechanism of olefin metathesis. The reaction involves the exchange of alkene fragments between the two reactants, leading to the formation of new carbon-carbon double bonds. The catalyst forms a metallacyclobutane intermediate, which rearranges to produce the products.
Step 3: Predict the products of the reaction. The terminal alkene groups from both reactants will interact, resulting in the formation of two new alkenes. One product will likely be a symmetrical or unsymmetrical alkene formed by the combination of the two reactants' alkene fragments.
Step 4: Consider the functional groups present in the reactants. Eugenol has a phenolic hydroxyl group and a methoxy group, while the diol has two hydroxyl groups. These functional groups remain intact during the metathesis reaction, as the reaction specifically targets the alkene groups.
Step 5: Draw the expected products. The new alkenes formed will reflect the exchange of alkene fragments between the reactants. Ensure that the connectivity of the carbon atoms and the functional groups is preserved in the products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Metathesis Reactions
Metathesis reactions involve the exchange of parts between two molecules, typically alkenes, resulting in the formation of new alkenes. This reaction is facilitated by catalysts, such as the Schrock or Grubbs catalysts, which stabilize the transition state and lower the activation energy. In the context of the provided question, eugenol and a diol reactant undergo metathesis to yield new products through the reorganization of their double bonds.
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Alkene Metathesis Concept 1
Schrock and Grubbs Catalysts
Schrock and Grubbs catalysts are types of transition metal complexes used to promote metathesis reactions. Schrock catalysts are typically based on molybdenum or tungsten, while Grubbs catalysts are based on ruthenium. These catalysts facilitate the breaking and forming of carbon-carbon double bonds, allowing for efficient and selective reactions, which are crucial for synthesizing complex organic molecules.
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Product Prediction in Organic Reactions
Predicting the products of organic reactions, such as metathesis, requires understanding the structure of the reactants and the mechanism of the reaction. In this case, the reaction between eugenol and the diol involves the formation of new alkenes through the exchange of alkyl groups. Analyzing the molecular structure and functional groups present helps in determining the likely products and their configurations.
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Related Practice
Textbook Question
Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.
(c)
(d)
2
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Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(b)
5
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Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(i)
5
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Textbook Question
Show how you might use olefin metathesis to assemble the following alkenes from smaller units:
(a)
(b)
1
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Textbook Question
Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.
(a)
(b)
1
views