Textbook Question
For each of the following alkynes, draw the products obtained from (1) the acid-catalyzed addition of water (mercuric ion is added for part a) and from (2) hydroboration–oxidation:
a. 1-butyne
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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 19a
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 19aChapter 8, Problem 19a
Describe the alkyne you should start with and the reagents you should use if you want to synthesize
a. pentane.
Verified step by step guidance1
Step 1: Understand the target molecule. Pentane is an alkane with five carbon atoms and no double or triple bonds. To synthesize pentane from an alkyne, you need to perform a reduction reaction that converts the alkyne into an alkane.
Step 2: Choose the starting alkyne. To ensure the final product is pentane, you should start with an alkyne that has five carbon atoms, such as 1-pentyne or 2-pentyne. Both are suitable starting materials.
Step 3: Select the reagents for the reduction. To fully reduce the alkyne to an alkane, you can use hydrogen gas (H₂) in the presence of a metal catalyst, such as palladium (Pd) or platinum (Pt). This process is known as catalytic hydrogenation.
Step 4: Perform the reaction. Subject the alkyne to hydrogen gas under pressure in the presence of the metal catalyst. The triple bond will be reduced to a single bond, resulting in the formation of pentane.
Step 5: Verify the product. After the reaction, confirm the structure of the product using techniques such as gas chromatography or NMR spectroscopy to ensure that the final compound is pentane.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkynes
Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are unsaturated compounds and can be represented by the general formula CnH2n-2. Understanding the structure and reactivity of alkynes is crucial for predicting the products of chemical reactions, especially in synthesis.
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Alkyne Hydration
Synthesis of Alkanes
The synthesis of alkanes, such as pentane, from alkynes typically involves hydrogenation or reduction reactions. This process can convert the triple bond of an alkyne into a single bond, resulting in an alkane. Identifying the correct reagents, such as hydrogen gas (H2) and a catalyst like palladium or platinum, is essential for achieving this transformation.
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02:47Functionalizing Alkanes
Reagents and Reaction Conditions
The choice of reagents and reaction conditions is critical in organic synthesis. For converting an alkyne to pentane, one might use lithium aluminum hydride (LiAlH4) for reduction or hydrogenation with a metal catalyst. Understanding how these reagents interact with alkynes helps in designing effective synthetic pathways to desired products.
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Related Practice
Textbook Question
Describe the alkyne you should start with and the reagents you should use if you want to synthesize
b. cis-2-butene.
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Textbook Question
Only one alkyne forms an aldehyde when it undergoes the mercuric-ion-catalyzed addition of water. Identify the alkyne.
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Textbook Question
What are products of the following reactions?
a.
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Textbook Question
Describe the alkyne you should start with and the reagents you should use if you want to synthesize
c. trans-2-pentene.
d. 1-hexene.
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Textbook Question
Which alkyne should be used for the synthesis of each of the following ketones?
c.
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