Textbook Question
What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl3?
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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 5
Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?
Verified step by step guidance1
Step 1: Recognize that muscalure is a long-chain alkene with a specific double bond position. Analyze its structure to determine the chain length and the location of the double bond.
Step 2: Plan the synthesis by identifying the need to elongate the carbon chain of 1-bromopentane. Use a coupling reaction, such as the Wurtz reaction, to combine two molecules of 1-bromopentane, forming a 10-carbon alkane (decane).
Step 3: Introduce a double bond into the decane chain. This can be achieved through a dehydrohalogenation reaction. First, convert decane into a halogenated intermediate (e.g., 1-bromodecane) using bromination, and then treat it with a strong base (e.g., KOH or NaOH) to eliminate HBr and form the desired alkene.
Step 4: Ensure the double bond is in the correct position to match the structure of muscalure. If necessary, use a method like isomerization to shift the double bond to the appropriate location.
Step 5: Purify the final product to isolate muscalure. Use techniques such as distillation or chromatography to ensure the product is free of impurities and matches the desired structure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of synthesizing muscalure from 1-bromopentane, understanding this mechanism is crucial, as it allows for the introduction of functional groups necessary for the final product. The reaction can proceed via either the SN1 or SN2 pathway, depending on the structure of the substrate and the conditions used.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Functional Group Transformation
Functional group transformation involves converting one functional group into another, which is essential in organic synthesis. In the case of muscalure, starting from 1-bromopentane, you may need to transform alkyl halides into alcohols or other functional groups that can be further modified. This concept is vital for understanding how to manipulate the molecular structure to achieve the desired compound.
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Stereochemistry
Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Muscalure has specific stereochemical requirements for its biological activity as a pheromone. When synthesizing muscalure from 1-bromopentane, it is important to consider the stereochemical outcomes of reactions to ensure that the correct isomer is produced, as different isomers can have vastly different effects.
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Related Practice
Textbook Question
What bromo-substituted compound would be required to react with (CH2=CH)2CuLi in order to form each of the following compounds?
c.
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Textbook Question
What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?
b. (CH3CH=CH)2CuLi
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Textbook Question
Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.
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Textbook Question
What bromo-substituted compound would be required to react with (CH2=CH)2CuLi in order to form each of the following compounds?
b.
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Textbook Question
Which is more reactive, an organolithium compound or an organosodium compound? Explain your answer.
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