Textbook Question
Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.
d.
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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 58e
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 58eChapter 17, Problem 58e
Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.
e. 
Verified step by step guidance1
Step 1: Analyze the given reaction. The starting material is a methyl ester (cyclohexanecarboxylic acid methyl ester), and the reagents are lithium aluminum hydride (LiAlH4) followed by acid workup (H3O+). LiAlH4 is a strong reducing agent used to reduce esters to primary alcohols.
Step 2: Understand the mechanism. LiAlH4 donates hydride ions (H-) to the carbonyl carbon of the ester, breaking the C=O bond and forming an intermediate alkoxide. The methoxy group (-OCH3) is displaced as methanol during the reaction.
Step 3: After the reduction by LiAlH4, the intermediate alkoxide is protonated during the acid workup (H3O+), resulting in the formation of a primary alcohol. The ester group is completely reduced to an alcohol.
Step 4: Identify the product. The ester group (-COOCH3) in cyclohexanecarboxylic acid methyl ester is reduced to a primary alcohol (-CH2OH), resulting in cyclohexanemethanol as the product.
Step 5: Classify the reaction. Since the reaction involves the addition of hydrogen (reduction of the ester to an alcohol), it is classified as a reduction reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reduction Reactions
Reduction reactions involve the gain of electrons or hydrogen, or the loss of oxygen by a molecule. In organic chemistry, this often pertains to the conversion of carbonyl compounds (like aldehydes and ketones) into alcohols. The reaction shown in the image illustrates the reduction of a carbonyl compound using lithium aluminum hydride (LiAlH4), a strong reducing agent.
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Reductive Amination
Lithium Aluminum Hydride (LiAlH4)
Lithium aluminum hydride is a powerful reducing agent commonly used in organic synthesis. It can reduce a variety of functional groups, including carbonyls and esters, to their corresponding alcohols. In the reaction depicted, LiAlH4 donates hydride ions (H-) to the carbonyl carbon, facilitating the reduction process.
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Protonation of Alkoxides
After the reduction step, the alkoxide intermediate formed needs to be protonated to yield the final alcohol product. This is typically achieved by adding a proton source, such as water or an acid, as shown in the second step of the reaction. This step is crucial as it converts the alkoxide into a stable alcohol, completing the reduction process.
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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.
f.
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Textbook Question
Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:
a.
b.
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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
Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:
c.
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Textbook Question
Which of the reactions cannot be used for the synthesis of isobutyl alcohol?
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