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 48a
What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?
a. 
Verified step by step guidance1
Analyze the target compound: The structure provided is a six-membered ring containing a ketone group and an alkene. This suggests that the compound was likely formed via ring-closing metathesis (RCM) of a diene precursor.
Identify the functional groups: The ketone group is already present in the ring, and the alkene is formed during the RCM reaction. The precursor must contain two terminal alkenes that will undergo metathesis to form the cyclic structure.
Determine the precursor structure: To synthesize this compound, the starting material should be a linear diene with two terminal alkenes. The ketone group should already be present in the linear precursor.
Propose the starting material: The starting material would be a linear molecule with the following structure: CH2=CH-(CH2)3-CO-(CH2)2-CH=CH2. This molecule contains two terminal alkenes and a ketone group positioned appropriately to form the six-membered ring upon ring-closing metathesis.
Explain the reaction mechanism: During ring-closing metathesis, the two terminal alkenes in the diene precursor react in the presence of a metathesis catalyst (e.g., Grubbs catalyst) to form the cyclic structure. The ketone group remains unchanged during the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ring-Closing Metathesis (RCM)
Ring-Closing Metathesis is a powerful synthetic method in organic chemistry that involves the formation of a ring by the exchange of alkene partners through the action of a catalyst, typically a transition metal complex. This reaction is particularly useful for synthesizing cyclic compounds from linear precursors, allowing for the creation of various ring sizes and functionalities.
Recommended video:
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Alkene Metathesis Concept 2
Starting Materials for RCM
The choice of starting materials in RCM is crucial, as they must contain two or more alkenes that can react to form a cyclic structure. Typically, these starting materials are diene or polyene compounds, which provide the necessary double bonds for the metathesis reaction to occur. The structure of the starting material directly influences the efficiency and selectivity of the ring formation.
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Guided course
02:49Aromatic synthesis starting with benzene/benzene derivatives
Catalysts in RCM
Catalysts play a vital role in Ring-Closing Metathesis by facilitating the metathesis reaction without being consumed in the process. Common catalysts include Grubbs and Hoveyda-Grubbs catalysts, which are based on ruthenium. The choice of catalyst can affect the reaction conditions, such as temperature and solvent, and ultimately the yield and purity of the desired cyclic product.
Recommended video:
2:10Introduction to Catalysis 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
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
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
For those compounds that can be prepared by a Heck reaction, what starting materials are required?
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