Domanda del libro di testo
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Capitolo 10, Problema 25d
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d) 
Guida verificata passo dopo passo1
Identify the functional group in the given compound. The structure shows a six-membered cyclic ketone (cyclohexanone) with a carbonyl group (C=O).
Understand the role of LiAlH4 (Lithium Aluminum Hydride). It is a strong reducing agent that reduces ketones to secondary alcohols by adding hydrogens to the carbonyl group.
Write the mechanism of the reaction. LiAlH4 donates a hydride ion (H⁻) to the carbonyl carbon, breaking the double bond and forming an alkoxide intermediate.
Perform hydrolysis. The alkoxide intermediate reacts with water during the hydrolysis step to form the final alcohol product.
Predict the product. The ketone (cyclohexanone) is reduced to a secondary alcohol (cyclohexanol) with the hydroxyl group (-OH) replacing the carbonyl group.
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Lithium Aluminum Hydride (LiAlH4) Reactivity
LiAlH4 is a strong reducing agent commonly used in organic chemistry to reduce carbonyl compounds, such as aldehydes and ketones, to their corresponding alcohols. It can also reduce esters and carboxylic acids, making it a versatile reagent in organic synthesis. Understanding its reactivity is crucial for predicting the products of reactions involving carbonyl-containing compounds.
Video consigliato:
01:42
LiAl(ot-Bu)3H on Acid Chlorides
Hydrolysis of Alkoxides
After the reduction of a carbonyl compound by LiAlH4, the resulting alkoxide intermediate can be hydrolyzed by adding water or an alcohol, such as methanol. This hydrolysis step converts the alkoxide into an alcohol, which is the final product of the reaction. Recognizing the role of hydrolysis is essential for determining the final products in reduction reactions.
Video consigliato:
Percorso guidato
3:09Hydrolysis of Thioesters Example 2
Solvent Effects in Organic Reactions
The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves as both a solvent and a reactant during hydrolysis. Understanding how solvents interact with reactants and products helps predict reaction mechanisms and product distributions, which is vital for accurately forecasting the results of the given reaction.
Video consigliato:
02:26General format of reactions and how to interpret solvents.
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