Textbook Question
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
2. 1-phenyl-2-butyn-1-ol
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
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. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 13a(1)
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 13a(1)Chapter 17, Problem 13a(1)
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
1. 1-pentyn-3-ol
Verified step by step guidance1
Step 1: Begin with ethyne (C₂H₂) as the starting material. Perform a reaction with sodium amide (NaNH₂) to generate the acetylide ion (C≡C⁻), which is a strong nucleophile.
Step 2: Perform an alkylation reaction by reacting the acetylide ion with 1-bromopropane (CH₃CH₂CH₂Br). This will extend the carbon chain, forming 1-butyne (CH≡C-CH₂CH₂CH₃).
Step 3: To introduce the hydroxyl group (-OH) at the desired position, perform a hydroboration-oxidation reaction. First, react 1-butyne with a bulky borane reagent, such as disiamylborane [(sia)₂BH], to ensure anti-Markovnikov addition of the boron atom.
Step 4: Oxidize the organoborane intermediate using hydrogen peroxide (H₂O₂) in the presence of a base (e.g., NaOH). This will replace the boron atom with a hydroxyl group, yielding 1-pentyn-3-ol.
Step 5: Verify the structure of the product to ensure that the hydroxyl group is located on the third carbon of the pentynyl chain, confirming the synthesis of 1-pentyn-3-ol.
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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 in synthetic pathways is crucial for preparing target compounds.
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Alkyne Reactions
Alkynes undergo a variety of reactions, including hydration, hydroboration, and oxidation. In the case of preparing 1-pentyn-3-ol, the hydration of an alkyne can be achieved through acid-catalyzed reactions, leading to the formation of alcohols. Familiarity with these reactions and their mechanisms is essential for constructing the desired compound from ethyne.
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Functional Group Transformation
Functional group transformations involve converting one functional group into another, which is a key strategy in organic synthesis. In this context, transforming an alkyne into an alcohol requires specific reagents and conditions. Understanding how to effectively perform these transformations is vital for synthesizing compounds like 1-pentyn-3-ol from ethyne.
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Related Practice
Textbook Question
Which of the following compounds does not form an alcohol when it reacts with excess Grignard reagent?
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Textbook Question
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
3. 2-methyl-3-hexyn-2-ol
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Textbook Question
Show how the following compounds can be synthesized from cyclohexanol.
a. b. c.
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Textbook Question
Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.
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Textbook Question
What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridinium chloride?
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