Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
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Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
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
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Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 46e
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 46eChapter 8, Problem 46e
How can the following compounds be prepared using ethyne as the starting material?
e. 
Verified step by step guidance1
Step 1: Begin with ethyne (C₂H₂) as the starting material. Ethyne is a simple alkyne with a triple bond between two carbon atoms.
Step 2: Perform hydrohalogenation of ethyne using HBr to form bromoethene (CH₂=CHBr). This reaction adds one equivalent of HBr across the triple bond, resulting in a vinyl halide.
Step 3: Carry out a Grignard reaction by reacting bromoethene with magnesium in dry ether to form the Grignard reagent, CH₂=CH-MgBr.
Step 4: React the Grignard reagent with an appropriate alkyl halide, such as ethyl bromide (CH₃CH₂Br), to form the desired compound. This step involves nucleophilic substitution, where the alkyl group is added to the vinyl group.
Step 5: Perform a final step to ensure the compound matches the structure provided in the image. This may involve purification or verification of the product structure using spectroscopic methods like NMR or IR.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ethyne as a Building Block
Ethyne, also known as acetylene, is a simple alkyne that serves as a versatile building block in organic synthesis. Its triple bond allows for various reactions, including addition reactions with electrophiles, which can lead to the formation of more complex molecules. Understanding how to manipulate ethyne's reactivity is crucial for synthesizing a wide range of organic compounds.
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Reactions of Alkynes
Alkynes undergo several key reactions, including hydrogenation, halogenation, and hydroboration-oxidation. These reactions can modify the triple bond to form double bonds or single bonds, allowing for the construction of different functional groups. Familiarity with these reaction mechanisms is essential for predicting the products when starting from ethyne.
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01:01General properties of double addition reactions to alkynes.
Functional Group Transformation
Functional group transformation involves converting one functional group into another through chemical reactions. This concept is vital in organic synthesis, as it allows chemists to create desired compounds from simpler starting materials like ethyne. Recognizing how to strategically change functional groups can facilitate the preparation of complex organic molecules.
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Related Practice
Textbook Question
Do the equilibria of the following acid–base reactions lie to the right or the left? (The pKa of H2O2 is 11.6.)
HOOH + HO− ⇌ HOO− + H2O
RC☰CH + HOO− ⇌ RC☰C− + HOOH
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
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Textbook Question
What is each compound's systematic name?
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
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