Textbook Question
Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2) to be more similar to the reactivity of an epoxide or to the reactivity of a noncyclic ether? Why?
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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 24e
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 24eChapter 11, Problem 24e
What are the major products obtained when each of the following ethers is heated with one equivalent of HI?
e. 
Verified step by step guidance1
Identify the structure of the ether in question. Ethers have the general formula R-O-R', where R and R' are alkyl or aryl groups. Determine the specific groups attached to the oxygen atom in the given ether.
Understand the reaction mechanism: When an ether reacts with HI, the bond between the oxygen and one of the alkyl groups (R or R') is cleaved. This occurs via an SN2 or SN1 mechanism, depending on the nature of the alkyl groups. Primary and secondary alkyl groups typically undergo SN2, while tertiary alkyl groups favor SN1.
Determine which bond will break: The bond between the oxygen and the less sterically hindered alkyl group (or the group that forms a more stable carbocation in the case of SN1) is more likely to break. This results in the formation of an alcohol (R-OH) and an alkyl iodide (R'-I).
Write the products: After the bond cleavage, one product will be an alcohol (R-OH) formed from the group still attached to the oxygen, and the other product will be an alkyl iodide (R'-I) formed from the group that was cleaved.
Verify the stoichiometry: Since one equivalent of HI is used, ensure that only one ether bond is cleaved, resulting in the formation of one molecule of alcohol and one molecule of alkyl iodide as the major products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ethers
Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. They are generally stable and non-reactive under normal conditions but can undergo cleavage in the presence of strong acids, such as hydroiodic acid (HI). Understanding the structure and reactivity of ethers is crucial for predicting the products formed during their reaction with HI.
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Acid-Catalyzed Cleavage
Acid-catalyzed cleavage of ethers involves the protonation of the ether oxygen, making the ether bond more susceptible to nucleophilic attack. When heated with HI, the ether is cleaved to form an alcohol and an alkyl iodide. This reaction is significant in organic synthesis as it allows for the generation of useful products from relatively stable starting materials.
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Reaction Mechanism
The reaction mechanism for ether cleavage by HI typically involves a bimolecular nucleophilic substitution (SN2) pathway. In this mechanism, the iodide ion acts as a nucleophile, attacking the carbon atom bonded to the ether oxygen after the ether is protonated. Understanding this mechanism is essential for predicting the major products and their formation during the reaction.
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Related Practice
Textbook Question
Explain why methyl propyl ether forms both methyl iodide and propyl iodide when it is heated with excess HI.
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Textbook Question
What are the major products obtained when each of the following ethers is heated with one equivalent of HI?
c.
d.
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Textbook Question
What are the major products obtained when the following ether is heated with one equivalent of HI?
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Textbook Question
What product is obtained from the reaction of each of the following alcohols with
c. the regents required for a Swern oxidation?
1. 3-pentanol
2. 1-pentanol
3. 2-methyl-2-pentanol
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Textbook Question
Explain why HF and HCl cannot be used to cleave ethers in an SN2 reaction.
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