Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(a)
833
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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 53
Show how you might use olefin metathesis to assemble the following alkenes from smaller units:
(a) 
(b) 
Verified step by step guidance1
Step 1: Identify the target alkene structure. The given structure is a long-chain alkene with a double bond in the middle. Olefin metathesis can be used to assemble this structure by combining smaller alkene units.
Step 2: Break the target alkene into two smaller alkene fragments. For example, the target alkene can be divided into two smaller alkenes, each containing half of the carbon chain length and a terminal double bond.
Step 3: Select appropriate starting materials. Choose two smaller alkenes that can undergo olefin metathesis to form the desired product. For instance, two terminal alkenes such as 1-hexene and 1-hexene can be used.
Step 4: Perform the olefin metathesis reaction. Use a suitable catalyst, such as Grubbs' catalyst, to facilitate the reaction. The catalyst will break and reform the double bonds, creating the desired product.
Step 5: Purify the product. After the reaction, isolate and purify the target alkene using techniques such as distillation or chromatography to ensure the desired structure is obtained.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Olefin Metathesis
Olefin metathesis is a chemical reaction that involves the exchange of alkene fragments to form new alkenes. This reaction is facilitated by catalysts, typically transition metal complexes, which enable the breaking and forming of carbon-carbon double bonds. It is a powerful tool in organic synthesis, allowing for the construction of complex molecules from simpler ones.
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Alkene Metathesis Concept 1
Alkene Structure and Reactivity
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, which significantly influences their reactivity. The presence of this double bond makes alkenes more reactive than alkanes, allowing them to participate in various reactions, including addition and metathesis. Understanding the structure of alkenes is crucial for predicting their behavior in chemical reactions.
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Catalysts in Organic Reactions
Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In olefin metathesis, specific catalysts, such as Grubbs or Schrock catalysts, are employed to facilitate the reaction between alkenes. The choice of catalyst can significantly affect the efficiency and selectivity of the reaction, making it essential to understand their role in organic synthesis.
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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)
628
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Textbook Question
Complete each synthesis by providing the structure of the major product at each step, including any important stereochemistry.
a.
1323
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Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(b)
696
views
Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(c)
602
views
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
views