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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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 46f
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 46fChapter 8, Problem 46f
How can the following compounds be prepared using ethyne as the starting material?
f. 
Verified step by step guidance1
Step 1: Begin with ethyne (C≡CH), which is a simple alkyne. Ethyne can undergo reactions to form longer carbon chains. The first step is to perform a reaction with sodium amide (NaNH₂) to generate the acetylide ion (C≡C⁻). This ion is highly nucleophilic and can be used for chain elongation.
Step 2: React the acetylide ion with an alkyl halide, such as ethyl bromide (CH₃CH₂Br), in an SN2 reaction. This will result in the formation of a new carbon-carbon bond, yielding a terminal alkyne (CH≡C-CH₂CH₃).
Step 3: Perform a hydrogenation reaction using Lindlar's catalyst (Pd/BaSO₄, quinoline) to partially reduce the alkyne to a cis-alkene (CH₂=CH-CH₂CH₃). This step is crucial for controlling the stereochemistry of the intermediate.
Step 4: Carry out a hydroboration-oxidation reaction using BH₃·THF followed by H₂O₂/NaOH. This converts the alkene into an alcohol (CH₃CH(OH)CH₂CH₃).
Step 5: Finally, perform a dehydration reaction using concentrated H₂SO₄ or POCl₃ to remove water and form the desired alkane structure (CH₃CH₂CH₂CH₃). This completes the synthesis of the target compound starting from ethyne.
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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 target compounds.
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Reactions of Alkynes
Alkynes undergo a variety of chemical reactions, including hydrogenation, halogenation, and hydroboration. 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 types is essential for predicting the pathways to synthesize desired compounds from ethyne.
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Functional Group Transformations
Functional group transformations involve converting one functional group into another, which is a key strategy in organic synthesis. By understanding how to perform these transformations, such as converting alkynes to alcohols or ketones, chemists can design synthetic routes to create complex molecules from simpler starting materials like ethyne.
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Related Practice
Textbook Question
What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?
a. 1. H2/Lindlar catalyst 2. Br2/CH2Cl2
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
c.
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
e.
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Textbook Question
What is each compound's systematic name?
c.
d.
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Textbook Question
How can the following compounds be prepared using ethyne as the starting material?
b.
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