Textbook Question
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d)
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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 25a
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
Verified step by step guidance1
Step 1: Recognize the functional group in the given compound. The compound CH3-(CH2)8-CHO contains an aldehyde functional group (-CHO) at the end of the carbon chain.
Step 2: Understand the role of LiAlH4 (Lithium Aluminum Hydride). LiAlH4 is a strong reducing agent that reduces aldehydes to primary alcohols by adding hydrogen atoms to the carbonyl group.
Step 3: Write the reduction reaction. The aldehyde group (-CHO) will be reduced to a primary alcohol (-CH2OH). The carbon chain remains unchanged during this process.
Step 4: Consider the hydrolysis step. After the reduction by LiAlH4, hydrolysis (usually with water or a weak acid) is performed to quench the reaction and ensure the formation of the alcohol product.
Step 5: Combine the steps to predict the product. The final product will be CH3-(CH2)8-CH2OH, which is a primary alcohol with the same carbon chain length as the starting aldehyde.
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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) as a Reducing Agent
LiAlH4 is a powerful 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 carbonyl carbon, resulting in the formation of an alcohol after the reaction. Understanding its reactivity is crucial for predicting the products of reactions involving carbonyl compounds.
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Reducing Agents
Hydrolysis of Alkoxides
After the reduction of an aldehyde 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, releasing the corresponding alkoxide ion. Recognizing this step is essential for determining the final product of the reaction sequence.
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Aldehyde Structure and Reactivity
Aldehydes, characterized by the functional group -CHO, are highly reactive due to the presence of a carbonyl group. In the given compound, CH3-(CH2)8-CHO, the long carbon chain influences the physical properties but does not hinder the reactivity of the carbonyl group. Understanding the structure and reactivity of aldehydes is vital for predicting the outcome of their reactions with reducing agents.
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Related Practice
Textbook Question
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
748
views
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)
868
views
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
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(f)
753
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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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