Textbook Question
Describe how each of the following compounds could be synthesized from the given starting material.
a.
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
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. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 79
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 79Chapter 11, Problem 79
When ethyl ether is heated with excess HI for several hours, the only organic product obtained is ethyl iodide. Explain why ethyl alcohol is not obtained as a product.
Verified step by step guidance1
Understand the reaction: When ethyl ether (C₂H₅-O-C₂H₅) is heated with excess HI, the ether undergoes cleavage due to the strong nucleophilic and acidic nature of HI. This reaction is known as acid-catalyzed cleavage of ethers.
Recognize the mechanism: The reaction proceeds via protonation of the ether oxygen by HI, forming an oxonium ion (C₂H₅-O⁺-C₂H₅). This step makes the ether more susceptible to nucleophilic attack.
Identify the nucleophile: The iodide ion (I⁻) acts as a strong nucleophile and attacks one of the ethyl groups, breaking the C-O bond and forming ethyl iodide (C₂H₅I) and ethanol (C₂H₅OH) as intermediates.
Explain why ethyl alcohol is not isolated: Ethanol (C₂H₅OH) formed in the intermediate step reacts further with excess HI. The hydroxyl group (-OH) in ethanol is replaced by an iodide ion (I⁻) through a substitution reaction, producing another molecule of ethyl iodide (C₂H₅I).
Conclude the reasoning: Due to the excess HI and the reactivity of ethanol with HI, ethyl alcohol is not obtained as a final product. Instead, all the organic material is converted into ethyl iodide (C₂H₅I).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ether Cleavage
Ethers, like ethyl ether, undergo cleavage when treated with strong acids such as hydroiodic acid (HI). This reaction involves the protonation of the ether oxygen, making it a better leaving group. The cleavage results in the formation of alkyl halides and alcohols, but the conditions can favor the formation of one product over another.
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Reactivity of Alkyl Halides
In the presence of excess HI, ethyl iodide is favored due to the reactivity of alkyl halides. Ethyl iodide can further react with HI to regenerate iodide ions and promote the cleavage of the ether. This reaction pathway leads to the exclusive formation of ethyl iodide rather than ethyl alcohol, which would require different conditions to form.
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Equilibrium and Reaction Conditions
The reaction conditions, including the excess of HI and prolonged heating, shift the equilibrium towards the formation of ethyl iodide. The high concentration of HI drives the reaction to completion, minimizing the formation of ethyl alcohol. In contrast, if the conditions were less extreme, both products could potentially form.
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Related Practice
Textbook Question
When the following seven-membered ring alcohol is dehydrated, three alkenes are formed. Propose a mechanism for their formation.
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Textbook Question
How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?
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Textbook Question
Propose a mechanism for each of the following reactions:
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Textbook Question
Propose a mechanism for each of the following reactions:
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Textbook Question
Ethylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.
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