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.
(e)
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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 26a
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
a. heptan-1-ol
Verified step by step guidance1
Identify the target molecule, heptan-1-ol, which is a primary alcohol with seven carbon atoms and a hydroxyl group (-OH) attached to the first carbon.
Determine the appropriate carbonyl compound that can be reduced to form heptan-1-ol. In this case, the corresponding carbonyl compound is heptanal (an aldehyde with the formula CH₃(CH₂)₅CHO).
Choose a suitable reducing agent for the reduction of the aldehyde to a primary alcohol. Common reducing agents include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄).
Write the reaction mechanism: The reducing agent donates a hydride ion (H⁻) to the carbonyl carbon of heptanal, converting the C=O bond into a C-OH bond. The reaction is typically carried out in a solvent like ethanol or ether.
Conclude the synthesis: After the reduction step, the product is heptan-1-ol. If LiAlH₄ is used, a hydrolysis step with water or dilute acid is required to complete the reaction.
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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
Reduction is a chemical reaction that involves the gain of electrons or hydrogen, or the loss of oxygen. In organic chemistry, carbonyl compounds, such as aldehydes and ketones, can be reduced to alcohols using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4). Understanding the mechanism of this reduction is crucial for synthesizing alcohols from carbonyl precursors.
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Types of Carbonyl Compounds
Carbonyl compounds include aldehydes and ketones, which are characterized by the presence of a carbonyl group (C=O). Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, while ketones have two carbon groups attached. Identifying the correct type of carbonyl compound to reduce is essential for synthesizing the desired alcohol, in this case, heptan-1-ol.
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Synthesis of Alcohols
The synthesis of alcohols from carbonyl compounds is a fundamental reaction in organic chemistry. For heptan-1-ol, the target alcohol, one would typically start with a suitable aldehyde, such as heptanal, which can be reduced to form the primary alcohol. Understanding the structural features of the target alcohol and the starting materials is key to successfully planning the synthesis.
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Related Practice
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)
891
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Textbook Question
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
(d)
816
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Textbook Question
Arrange the following compounds in order of decreasing acidity.
CH3COOH, CH3OH, CH3CH3, CH3SO3H, CH3NH2, CH3SH, CH3C≡CH
1124
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Textbook Question
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
c. 2-methylhexan-3-ol
1222
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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
1518
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