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(3)
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 13a(3)Chapter 17, Problem 13a(3)
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
3. 2-methyl-3-hexyn-2-ol
Verified step by step guidance1
Step 1: Start with ethyne (C₂H₂) as the base molecule. Ethyne is a simple alkyne with a triple bond between two carbon atoms. The goal is to build the desired structure step by step by adding the necessary groups.
Step 2: Perform a hydroboration-oxidation reaction to convert ethyne into an aldehyde. Use reagents such as disiamylborane (R₂BH) followed by hydrogen peroxide (H₂O₂) and sodium hydroxide (NaOH). This will yield acetaldehyde (CH₃CHO).
Step 3: Perform an aldol addition reaction to extend the carbon chain. React acetaldehyde with a suitable aldehyde or ketone (e.g., butanal) in the presence of a base (e.g., NaOH) to form a β-hydroxy ketone intermediate. This step helps in building the hexyn backbone.
Step 4: Introduce the triple bond at the desired position. Use a strong base (e.g., NaNH₂) to deprotonate the β-hydroxy ketone intermediate, followed by elimination to form the alkyne. This will yield 2-methyl-3-hexyne.
Step 5: Perform a hydration reaction to introduce the hydroxyl group (-OH) at the desired position. Use reagents such as HgSO₄ and H₂SO₄ to hydrate the alkyne selectively, forming 2-methyl-3-hexyn-2-ol as the final product.
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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 is crucial for synthesizing target compounds like 2-methyl-3-hexyn-2-ol.
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Alkyne Reactions
Alkynes undergo a variety of reactions, including hydrohalogenation, hydration, and alkylation. These reactions can be used to introduce functional groups or extend carbon chains. For the synthesis of 2-methyl-3-hexyn-2-ol, knowledge of how to perform these reactions with ethyne is essential to achieve the desired structure and functionalization.
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Functional Group Interconversion
Functional group interconversion involves transforming one functional group into another, which is often necessary in organic synthesis. In the case of 2-methyl-3-hexyn-2-ol, converting an alkyne to an alcohol through hydration is a key step. Understanding the mechanisms and conditions for these transformations is vital for successfully preparing the target compound.
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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:
1. 1-pentyn-3-ol
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Textbook Question
Which of the following secondary alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?
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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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