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)
3
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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 24c
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
Verified step by step guidance1
Step 1: Identify the functional group in the given compound. The compound Ph-COOH contains a carboxylic acid functional group (-COOH) attached to a benzene ring (Ph).
Step 2: Recall the reactivity of NaBH4. Sodium borohydride (NaBH4) is a mild reducing agent that typically reduces aldehydes and ketones to their corresponding alcohols but does not reduce carboxylic acids under standard conditions.
Step 3: Consider the solvent. The reaction is stated to occur in methanol, which does not alter the reducing ability of NaBH4 toward carboxylic acids. Carboxylic acids are generally resistant to reduction by NaBH4.
Step 4: Predict the outcome. Since NaBH4 does not reduce carboxylic acids, the compound Ph-COOH will remain unchanged in this reaction.
Step 5: Conclude the reaction. The product of the reaction will be the same as the starting material, Ph-COOH, because NaBH4 does not affect carboxylic acids under these conditions.
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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) to alcohols. Sodium borohydride (NaBH4) is a common reducing agent that selectively reduces carbonyl compounds, making it essential to understand its reactivity in predicting products.
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Reductive Amination
Sodium Borohydride (NaBH4)
Sodium borohydride is a mild reducing agent commonly used in organic synthesis. It is particularly effective for reducing aldehydes and ketones to their corresponding alcohols, but it does not typically reduce carboxylic acids directly. Understanding its selectivity and the conditions under which it operates is crucial for predicting the outcome of reactions involving NaBH4.
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Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are generally more oxidized than aldehydes and ketones, making them less reactive towards mild reducing agents like NaBH4. In the context of the question, recognizing that NaBH4 does not reduce carboxylic acids directly is key to predicting the reaction products.
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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)
1
views
Textbook Question
Point out the flaws in the following incorrect Grignard syntheses.
(c)
(d)
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.
(a) CH3–(CH2)8–CHO
1
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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)
4
views
Textbook Question
Point out the flaws in the following incorrect Grignard syntheses.
(b)
1
views