Textbook Question
What alcohols are obtained from the reduction of the following compounds with sodium borohydride?
c. 4-tert-butylcyclohexanone
d. acetophenone
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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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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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 DerivativesProblem 20a,b
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 20a,bChapter 17, Problem 20a,b
What alcohols are obtained from the reduction of the following compounds with sodium borohydride?
a. 2-methylpropanal
b. cyclohexanone
Verified step by step guidance1
Identify the functional group in each compound. For 2-methylpropanal, the functional group is an aldehyde (-CHO). For cyclohexanone, the functional group is a ketone (C=O).
Understand the role of sodium borohydride (NaBH₄). It is a reducing agent that selectively reduces aldehydes and ketones to their corresponding alcohols by adding hydrogen atoms to the carbonyl group.
For 2-methylpropanal, the aldehyde group (-CHO) will be reduced to a primary alcohol (-CH₂OH). The carbonyl carbon gains a hydrogen atom, and the oxygen is converted to a hydroxyl group (-OH).
For cyclohexanone, the ketone group (C=O) will be reduced to a secondary alcohol (-CHOH). The carbonyl carbon gains a hydrogen atom, and the oxygen is converted to a hydroxyl group (-OH).
Write the structures of the resulting alcohols. For 2-methylpropanal, the product is 2-methyl-1-propanol. For cyclohexanone, the product is cyclohexanol. Ensure you understand how the reduction process changes the functional group in each case.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like aldehydes and ketones) into alcohols. Sodium borohydride (NaBH4) is a common reducing agent used for this purpose, effectively adding hydrogen to the carbonyl carbon.
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Aldehydes and Ketones
Aldehydes and ketones are two classes of carbonyl compounds. Aldehydes, such as 2-methylpropanal, have the carbonyl group (C=O) at the end of the carbon chain, while ketones, like cyclohexanone, have it within the chain. Understanding their structure is crucial for predicting the products of reduction reactions, as the position of the carbonyl group influences the resulting alcohol's structure.
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Sodium Borohydride as a Reducing Agent
Sodium borohydride is a selective and mild reducing agent commonly used in organic synthesis. It effectively reduces aldehydes and ketones to their corresponding alcohols without affecting other functional groups. Its mechanism involves the transfer of a hydride ion (H-) to the carbonyl carbon, leading to the formation of an alcohol, which is essential for understanding the products of the given reduction reactions.
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Related Practice
Textbook Question
Can a cyanohydrin be prepared by treating a ketone with sodium cyanide?
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Textbook Question
What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid?
a. ethyl butanoate
b. benzoic acid
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Textbook Question
Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.
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Textbook Question
What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridinium chloride?
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Textbook Question
What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid?
c. methyl benzoate
d. pentanoic acid
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