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.
(e) cyclodecyne
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 23d
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.
(d) 2-methylhex-3-yne
Verified step by step guidance1
Step 1: Understand the reactivity of the alkyne (2-methylhex-3-yne) with KMnO4. Neutral KMnO4 (dilute) is a mild oxidizing agent that adds hydroxyl groups across the triple bond, forming a diol. Warm, basic KMnO4 followed by acid is a stronger oxidizing agent that cleaves the triple bond, producing carboxylic acids.
Step 2: For reaction with dilute, neutral KMnO4, identify the triple bond in 2-methylhex-3-yne. The triple bond is between carbons 3 and 4. Neutral KMnO4 will add hydroxyl groups (-OH) to both carbons of the triple bond, resulting in a vicinal diol (a compound with two hydroxyl groups on adjacent carbons).
Step 3: For reaction with warm, basic KMnO4 followed by acid, the triple bond undergoes oxidative cleavage. This means the triple bond is broken, and each carbon of the triple bond is oxidized to a carboxylic acid. Identify the groups attached to carbons 3 and 4 to determine the resulting carboxylic acids.
Step 4: Analyze the structure of 2-methylhex-3-yne. Carbon 3 is bonded to a methyl group and a hydrogen, while carbon 4 is bonded to a propyl group and a hydrogen. Upon oxidative cleavage, carbon 3 will form acetic acid (CH3COOH), and carbon 4 will form butanoic acid (CH3CH2CH2COOH).
Step 5: Summarize the products. For dilute, neutral KMnO4, the product is a vicinal diol. For warm, basic KMnO4 followed by acid, the products are acetic acid and butanoic acid. Ensure to draw the structures of the products for clarity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, these reactions often lead to the formation of alcohols, ketones, or carboxylic acids. Understanding how different oxidizing agents, like KMnO4, interact with various functional groups is crucial for predicting the products of these reactions.
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Benzylic Oxidation
KMnO4 as an Oxidizing Agent
Potassium permanganate (KMnO4) is a strong oxidizing agent used in organic synthesis. In dilute, neutral conditions, it typically oxidizes alkynes to form cis-diol products, while in warm basic conditions followed by acid treatment, it can cleave alkynes to yield carboxylic acids. Recognizing the conditions under which KMnO4 operates helps in predicting the outcome of reactions.
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Alkyne Reactivity
Alkynes, characterized by carbon-carbon triple bonds, exhibit unique reactivity patterns compared to alkenes and alkanes. They can undergo various reactions, including oxidation, which can lead to the formation of different functional groups. Understanding the structure and reactivity of 2-methylhex-3-yne is essential for predicting the products when treated with KMnO4.
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Related Practice
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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Textbook Question
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.
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Textbook Question
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.
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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
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.
(c) hex-3-yne
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