Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(a)
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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 52b
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(b) 
Verified step by step guidance1
Step 1: Identify the type of metathesis reaction. In this case, the reaction involves a cyclic compound with two double bonds and a catalyst, which suggests a ring-closing metathesis (RCM) reaction.
Step 2: Analyze the structure of the cyclic compound. The molecule contains two double bonds and ester functional groups. These double bonds are positioned in a way that allows for the formation of a smaller ring upon reaction.
Step 3: Understand the role of the catalyst. The Schrock or Grubbs catalyst facilitates the breaking and reforming of carbon-carbon double bonds, enabling the formation of new rings or rearrangements.
Step 4: Predict the product. The reaction will likely result in the formation of a smaller cyclic compound with a single double bond, as the two double bonds in the starting material undergo metathesis to form a new bond.
Step 5: Consider stereochemistry and functional groups. The product will retain the ester groups and may exhibit cis/trans isomerism depending on the reaction conditions and the specific catalyst used.
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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 involving alkenes. In organic chemistry, this process is facilitated by catalysts such as the Schrock or Grubbs catalysts, which help to break and form double bonds, leading to the formation of new compounds. Understanding the mechanism of metathesis is crucial for predicting the products of the reaction.
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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 tungsten or molybdenum, while Grubbs catalysts are based on ruthenium. Each catalyst has unique properties that influence the reaction conditions and the types of products formed, making them essential for successful metathesis in synthetic organic chemistry.
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2:10Introduction to Catalysis Concept 1
Cyclic Compounds in Metathesis
Cyclic compounds, such as the one depicted in the image, can participate in metathesis reactions, leading to the formation of new cyclic or acyclic products. The strain in cyclic compounds can affect the reaction pathway and the stability of the products. Recognizing how the structure of the starting material influences the outcome of the reaction is vital for predicting the products in metathesis.
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1:41Alkene Metathesis Example 4
Related Practice
Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(i)
1251
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Textbook Question
Show how you might use olefin metathesis to assemble the following alkenes from smaller units:
(a)
(b)
918
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Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(c)
602
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Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(h)
1038
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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)
937
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