Textbook Question
a. 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(1)
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 57a(1)Chapter 17, Problem 57a(1)
Show the reagents required to form the primary alcohol in each of the following reactions.
Verified step by step guidance1
Step 1: Identify the starting material and the product. The starting material is an aldehyde (butanal), and the product is a primary alcohol (butanol).
Step 2: Recognize the type of reaction. This is a reduction reaction where the aldehyde functional group is reduced to a primary alcohol.
Step 3: Select the appropriate reducing agent. Common reducing agents for this transformation include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄).
Step 4: Choose the solvent. For NaBH₄, a protic solvent like ethanol or water is typically used. For LiAlH₄, an aprotic solvent like diethyl ether is required due to its reactivity.
Step 5: Write the reaction conditions. For example, if using NaBH₄, the reaction would proceed under mild conditions with ethanol as the solvent, converting butanal to butanol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reduction of Carbonyl Compounds
The conversion of carbonyl compounds (aldehydes or ketones) to alcohols involves a reduction reaction. This process typically requires a reducing agent, which donates electrons to the carbonyl carbon, resulting in the formation of an alcohol. In the case of aldehydes, the product is a primary alcohol, while ketones yield secondary alcohols.
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Common Reducing Agents
Common reducing agents used in organic chemistry for the reduction of carbonyl compounds include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). LiAlH4 is a strong reducing agent capable of reducing both aldehydes and ketones, while NaBH4 is milder and typically used for aldehydes and some ketones, making it a safer option in many laboratory settings.
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Mechanism of Reduction
The mechanism of reduction of carbonyl compounds involves nucleophilic attack by the hydride ion (H-) from the reducing agent on the electrophilic carbon of the carbonyl group. This leads to the formation of an alkoxide intermediate, which can then be protonated by water or an acid to yield the corresponding alcohol. Understanding this mechanism is crucial for predicting the outcome of the reaction.
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Related Practice
Textbook Question
Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.
a.
b.
c.
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Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
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Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
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Textbook Question
Which of the reactions cannot be used for the synthesis of isobutyl alcohol?
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Textbook Question
a. Show the reagents required to form the primary alcohol in each of the following reactions.
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