Textbook Question
Show the reagents required to form the primary alcohol in each of the following reactions.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
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. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 57a(8)
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 57a(8)Chapter 17, Problem 57a(8)
a. Show the reagents required to form the primary alcohol in each of the following reactions.
Verified step by step guidance1
Step 1: Analyze the reaction. The starting material is an ether (CH3CH2OCH2CH3), and the products are a primary alcohol (CH3CH2OH) and an alkyl iodide (CH3CH2I). This suggests a cleavage of the ether bond.
Step 2: Recognize the type of reaction. Ether cleavage typically occurs under acidic conditions with a strong nucleophile. In this case, the nucleophile is iodide (I⁻), which comes from HI (hydroiodic acid).
Step 3: Identify the reagents. The reagent required for this reaction is concentrated hydroiodic acid (HI), which provides both the acidic environment and the iodide nucleophile.
Step 4: Describe the mechanism. The ether undergoes protonation by HI, making the oxygen more electrophilic. This facilitates the cleavage of the C-O bond, forming the primary alcohol and alkyl iodide.
Step 5: Note the regioselectivity. In this reaction, the cleavage occurs to produce the more stable carbocation intermediate, ensuring the formation of the primary alcohol and alkyl iodide as products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ether Cleavage
Ether cleavage is a reaction where an ether is broken down into two alcohols or an alcohol and an alkyl halide. This process typically requires strong acids, such as HI or HBr, which protonate the ether oxygen, making it more susceptible to nucleophilic attack. The cleavage results in the formation of a primary alcohol and an alkyl halide, as shown in the provided reaction.
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Primary Alcohol Formation
A primary alcohol is characterized by having the hydroxyl (-OH) group attached to a carbon atom that is bonded to only one other carbon atom. In the context of ether cleavage, the reaction conditions and the choice of reagents are crucial for ensuring that the resulting alcohol is primary. This is important for understanding the selectivity of the reaction and the stability of the intermediates formed during the process.
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Reagents for Ether Cleavage
The choice of reagents is essential for ether cleavage reactions. Common reagents include hydroiodic acid (HI) and hydrobromic acid (HBr), which provide the necessary protons to initiate the cleavage. These reagents not only facilitate the breaking of the ether bond but also help in the formation of the primary alcohol and the corresponding alkyl halide, as depicted in the reaction diagram.
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Related Practice
Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
1
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Textbook Question
Draw the structure of two esters that will be reduced to propanol and butanol by LiAlH4 (followed by addition of aqueous acid).
Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
1
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Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
2
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Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
1
views