Textbook Question
Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.
(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)
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 23e
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
Verified step by step guidance1
Identify the functional group in cyclodecyne. Cyclodecyne is an alkyne, which contains a triple bond between two carbon atoms in a 10-membered ring structure.
Understand the reaction with dilute, neutral KMnO4. This reagent typically adds hydroxyl groups (-OH) across the triple bond, resulting in a dihydroxylated intermediate (a vicinal diol).
Understand the reaction with warm, basic KMnO4 followed by dilute acid. Under these conditions, the triple bond undergoes oxidative cleavage, breaking the bond completely and forming carboxylic acids at the ends of the cleaved bond.
Apply the oxidative cleavage to cyclodecyne. Since the triple bond is part of a ring, breaking it will open the ring, resulting in a linear structure with carboxylic acid groups at both ends.
Summarize the products: (1) Reaction with dilute, neutral KMnO4 produces a vicinal diol. (2) Reaction with warm, basic KMnO4 followed by dilute acid produces a dicarboxylic acid (a linear molecule with carboxylic acid groups at both ends).
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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 reagents, like KMnO4, act as oxidizing agents is crucial for predicting the products of reactions involving unsaturated hydrocarbons.
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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 alkenes and alkynes to form diols, while in warm basic conditions, it can cleave double or triple bonds, leading to the formation of carboxylic acids or ketones. The specific conditions dictate the extent and type of oxidation that occurs.
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Cyclodecyne Structure and Reactivity
Cyclodecyne is a cyclic alkyne with a triple bond in its structure, which makes it more reactive than alkenes or alkanes. The presence of the triple bond allows for various reactions, including oxidation. Understanding the structure and reactivity of cyclodecyne is essential for predicting the products formed when it undergoes treatment with KMnO4 under different conditions.
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Related Practice
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.
(d) 2-methylhex-3-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.
(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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