Textbook Question
Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO4 and (2) warm basic KMnO4, then dilute acid.
(a) hex-1-yne
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Ch.9 - Alkynes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 9, Problem 21d
For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation.
d. cyclodecyne
Verified step by step guidance1
Step 1: Analyze the structure of cyclodecyne. Cyclodecyne is a cyclic alkyne with a triple bond in a 10-membered ring. The triple bond is the reactive site for both hydration reactions.
Step 2: For HgSO4/H2SO4-catalyzed hydration, the reaction proceeds via Markovnikov addition. The triple bond is converted into a ketone. The mechanism involves the formation of an enol intermediate, which tautomerizes to a ketone. Identify the carbon atoms involved in the triple bond and predict the ketone product.
Step 3: For hydroboration-oxidation, the reaction proceeds via anti-Markovnikov addition. The triple bond is converted into an aldehyde. The mechanism involves the addition of BH3 (or a borane derivative) to the triple bond, followed by oxidation with H2O2/NaOH. Identify the carbon atoms involved in the triple bond and predict the aldehyde product.
Step 4: Compare the regioselectivity of the two reactions. HgSO4/H2SO4 hydration adds water in a Markovnikov fashion, favoring the more substituted carbon for the ketone formation. Hydroboration-oxidation adds water in an anti-Markovnikov fashion, favoring the less substituted carbon for the aldehyde formation.
Step 5: Draw the expected products for both reactions. For HgSO4/H2SO4 hydration, the product is a ketone at the more substituted carbon of the triple bond. For hydroboration-oxidation, the product is an aldehyde at the less substituted carbon of the triple bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Catalytic Hydration
Catalytic hydration involves the addition of water to an alkene in the presence of an acid catalyst, such as HgSO4 or H2SO4. This reaction typically follows Markovnikov's rule, where the more substituted carbon atom receives the hydroxyl group, leading to the formation of an alcohol. Understanding this mechanism is crucial for predicting the products of hydration reactions.
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09:11
Alkyne Hydration
Hydroboration-Oxidation
Hydroboration-oxidation is a two-step reaction that converts alkenes into alcohols. In the first step, borane (BH3) adds to the alkene in a syn addition, resulting in a trialkylborane intermediate. The second step involves oxidation with hydrogen peroxide (H2O2) in a basic solution, which replaces the boron with a hydroxyl group, yielding an alcohol. This reaction also follows anti-Markovnikov selectivity.
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06:38General properties of hydroboration-oxidation.
Cyclodecyne Structure
Cyclodecyne is a cyclic alkyne with a ten-membered ring structure containing a triple bond. Its unique structure influences its reactivity and the types of products formed during chemical reactions. Understanding the geometry and strain of cyclodecyne is essential for predicting the outcomes of hydration and hydroboration-oxidation reactions, as these factors can affect regioselectivity and stereochemistry.
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Related Practice
Textbook Question
Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamyl groups. Disiamylborane is prepared by the reaction of BH3·THF with an alkene.
a. Draw the structural formulas of the reagents and the products in the preparation of disiamylborane.
b. Explain why the reaction in part (a) goes only as far as the dialkylborane. Why is Sia3B not formed?
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Textbook Question
For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation.
c. hex-3-yne
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Textbook Question
For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation.
b. hex-2-yne
Textbook Question
Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO4 and (2) warm basic KMnO4, then dilute acid.
(b) hex-2-yne
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Textbook Question
For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation.
a. hex-1-yne