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 24a
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.
(a) CH3–(CH2)8–CHO
Verified step by step guidance1
Step 1: Recognize the type of reaction. Sodium borohydride (NaBH4) is a reducing agent commonly used to reduce aldehydes and ketones to their corresponding alcohols. Methanol serves as the solvent in this reaction.
Step 2: Identify the functional group in the given compound. The compound CH3-(CH2)8-CHO contains an aldehyde group (-CHO) at the end of the carbon chain.
Step 3: Understand the mechanism of the reduction. NaBH4 donates a hydride ion (H⁻) to the carbonyl carbon of the aldehyde group. This breaks the double bond between the carbon and oxygen, forming an alkoxide intermediate.
Step 4: Protonation of the alkoxide intermediate. The alkoxide ion formed in the previous step is protonated by methanol (the solvent), resulting in the formation of a primary alcohol.
Step 5: Predict the product. The aldehyde group (-CHO) in CH3-(CH2)8-CHO is reduced to a primary alcohol (-CH2OH), yielding CH3-(CH2)8-CH2OH as the final product.
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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 groups (like aldehydes and ketones) into alcohols. Sodium borohydride (NaBH4) is a common reducing agent that effectively reduces aldehydes to primary alcohols.
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Reductive Amination
Sodium Borohydride (NaBH4)
Sodium borohydride is a mild reducing agent used primarily for the reduction of aldehydes and ketones to their corresponding alcohols. It is less reactive than lithium aluminum hydride, making it suitable for selective reductions in various solvents, including methanol. Its ability to donate hydride ions (H-) is crucial for the reduction process.
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Aldehyde Structure and Reactivity
Aldehydes are characterized by the presence of a carbonyl group (C=O) bonded to at least one hydrogen atom. This structure makes them more reactive than ketones, as they can be easily reduced to alcohols. In the given compound, CH3-(CH2)8-CHO, the aldehyde group is at the terminal position, making it a primary aldehyde that will yield a primary alcohol upon reduction.
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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.
(c) Ph-COOH
3
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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.
(e)
1
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Textbook Question
Point out the flaws in the following incorrect Grignard syntheses.
(c)
(d)
3
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Textbook Question
Point out the flaws in the following incorrect Grignard syntheses.
(a)
1
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Textbook Question
Point out the flaws in the following incorrect Grignard syntheses.
(b)
1
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