Textbook Question
Which of the following compounds cannot be prepared by a Heck reaction?
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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 45a
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
Verified step by step guidance1
Step 1: Understand the concept of alkene metathesis. Alkene metathesis is a reaction where two alkenes exchange their alkylidene groups, forming new alkenes. The reaction is catalyzed by metal carbene complexes, and the product distribution depends on the stability and symmetry of the resulting alkenes.
Step 2: Analyze the given sets of alkenes. For each pair, consider the possible products of the metathesis reaction. The reaction involves breaking the double bonds of the alkenes and recombining the fragments to form new alkenes.
Step 3: Evaluate the stability of the potential products. The highest yield of a single alkene is achieved when the reaction favors the formation of a single, thermodynamically stable product. Symmetry and substitution patterns of the alkenes play a key role in determining the product distribution.
Step 4: For each pair of alkenes: (1) 1-butene and 1-pentene, (2) 2-butene and 3-hexene, and (3) 2-butene and 1-pentene, write the possible products of the metathesis reaction. Consider the substitution patterns of the resulting alkenes and their relative stabilities (e.g., more substituted alkenes are generally more stable).
Step 5: Compare the product distributions for each pair. Identify the pair that leads to the formation of a single, stable alkene as the major product. This pair will correspond to the highest yield of a single alkene.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkene Metathesis
Alkene metathesis is a chemical reaction that involves the exchange of alkyl groups between alkenes, leading to the formation of new alkenes. This reaction is facilitated by catalysts, such as those based on molybdenum or tungsten, and is significant in organic synthesis for producing higher-value compounds. Understanding the mechanism and factors influencing the reaction is crucial for predicting the outcomes of different alkene combinations.
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Alkene Metathesis Concept 1
Thermodynamic Stability of Alkenes
The stability of alkenes is influenced by their degree of substitution; more substituted alkenes are generally more stable due to hyperconjugation and the inductive effect. In metathesis, the formation of more stable alkenes typically leads to higher yields. Recognizing the stability of the potential products formed from the metathesis reaction helps in determining which alkene pair will yield the most favorable outcome.
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04:28Understanding trends of alkene stability.
Selectivity in Metathesis Reactions
Selectivity in metathesis reactions refers to the preference for forming certain products over others based on the starting materials. Factors such as sterics, electronic effects, and the nature of the catalyst can influence selectivity. Analyzing the structure of the alkenes involved allows chemists to predict which combinations will yield a single, predominant alkene, thus maximizing the efficiency of the reaction.
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Related Practice
Textbook Question
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.
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Textbook Question
Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
b.
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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
For those compounds that can be prepared by a Heck reaction, what starting materials are required?
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