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 15c
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 15cChapter 8, Problem 15c
Which alkyne should be used for the synthesis of each of the following ketones?
c. 
Verified step by step guidance1
Step 1: Analyze the target ketone structure. The given ketone has a methyl group (CH₃) attached to the carbonyl group (C=O), and the other side of the carbonyl group is bonded to a cyclohexyl group (a six-membered ring).
Step 2: Recall the general mechanism for synthesizing ketones from alkynes. Ketones can be synthesized via the hydration of alkynes using acid-catalyzed conditions (H₂SO₄, H₂O) and a mercury(II) sulfate catalyst (HgSO₄). This reaction follows Markovnikov's rule, where the OH group adds to the more substituted carbon of the triple bond.
Step 3: Determine the alkyne precursor. To form the given ketone, the alkyne must have a triple bond between the carbon that will become the carbonyl group and the carbon that will be bonded to the cyclohexyl group. The alkyne should be 1-cyclohexyl-1-propyne.
Step 4: Explain the hydration process. When 1-cyclohexyl-1-propyne undergoes hydration in the presence of H₂SO₄ and HgSO₄, the OH group adds to the more substituted carbon (the carbon bonded to the cyclohexyl group), and the triple bond is converted into a double bond, forming an enol intermediate. The enol tautomerizes to the ketone.
Step 5: Verify the structure. After hydration and tautomerization, the final product matches the target ketone structure, with the methyl group and cyclohexyl group attached to the carbonyl carbon.
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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 participate in various chemical reactions, including addition reactions. Understanding the structure and reactivity of alkynes is crucial for predicting the products of reactions involving them, especially in synthetic pathways.
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Alkyne Hydration
Ketone Synthesis
Ketones are organic compounds characterized by a carbonyl group (C=O) flanked by two carbon atoms. The synthesis of ketones often involves the reaction of alkynes with specific reagents, such as water in the presence of a catalyst, to yield the desired ketone. Familiarity with the mechanisms of these reactions is essential for determining the appropriate alkyne for a given ketone.
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Reagents and Reaction Conditions
The choice of reagents and reaction conditions significantly influences the outcome of organic reactions. For synthesizing ketones from alkynes, reagents like water, acids, or specific catalysts are often employed. Understanding how these factors affect the reaction pathway is vital for successfully identifying the correct alkyne for the synthesis of the desired ketone.
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Related Practice
Textbook Question
Drawing on what you know about the stereochemistry of alkene addition reactions,
b. predict the configuration of the product of the reaction.
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Textbook Question
What ketones are formed from the acid-catalyzed hydration of 3-heptyne?
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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
Describe the alkyne you should start with and the reagents you should use if you want to synthesize
a. pentane.
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Textbook Question
Which alkyne should be used for the synthesis of each of the following ketones?
a.
b.
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