Textbook Question
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)
2
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- 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
Chapter 10, Problem 25e
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) 
Verified step by step guidance1
Step 1: Analyze the structure of the compound provided. The molecule contains three carbonyl groups: an aldehyde (-CHO), a ketone (C=O), and an ester (-COOCH3). Each of these functional groups reacts differently with LiAlH4.
Step 2: Understand the role of LiAlH4 (Lithium Aluminum Hydride). It is a strong reducing agent that reduces aldehydes, ketones, and esters to their corresponding alcohols. The reaction typically involves the addition of hydride ions (H-) to the carbonyl carbon.
Step 3: Predict the reduction of the aldehyde group (-CHO). LiAlH4 will reduce the aldehyde to a primary alcohol (-CH2OH). This occurs because the hydride ion attacks the carbonyl carbon, followed by protonation during hydrolysis.
Step 4: Predict the reduction of the ketone group (C=O). LiAlH4 will reduce the ketone to a secondary alcohol (-CHOH). The hydride ion attacks the carbonyl carbon, and hydrolysis provides the proton to complete the alcohol formation.
Step 5: Predict the reduction of the ester group (-COOCH3). LiAlH4 reduces esters to primary alcohols. The ester group will be cleaved, producing methanol (CH3OH) and a primary alcohol derived from the remaining carbon chain. Hydrolysis ensures the completion of the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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 donates hydride ions (H-) to the electrophilic carbon of the carbonyl group, facilitating the conversion of the carbonyl compound into an alcohol. Understanding its reactivity is crucial for predicting the products of reactions involving carbonyl-containing compounds.
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LiAl(ot-Bu)3H on Acid Chlorides
Hydrolysis of Alkoxides
After the reduction of a carbonyl compound by LiAlH4, the resulting alkoxide intermediate can undergo hydrolysis when treated with water or an alcohol like methanol. This process involves the protonation of the alkoxide to form the corresponding alcohol. Recognizing the hydrolysis step is essential for determining the final products of the reaction sequence.
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Solvent Effects in Organic Reactions
The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves both as a solvent and as a reactant during hydrolysis. Understanding how solvents can stabilize intermediates, affect reaction rates, and participate in reactions is important for accurately predicting the products of the reaction sequence involving LiAlH4 and hydrolysis.
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Related Practice
Textbook Question
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
(d)
1
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Textbook Question
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
c. 2-methylhexan-3-ol
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Textbook Question
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.
(c) Ph-COOH
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Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
a. heptan-1-ol
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Textbook Question
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.
(a) CH3–(CH2)8–CHO
1
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