Domanda del libro di testo
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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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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 DerivativesProblema 58e
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 58eCapitolo 16, Problema 58e
Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.
e. 
Guida verificata passo dopo passo1
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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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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