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 24e
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) 
Verified step by step guidance1
Step 1: Identify the functional groups in the given compound. The structure contains three carbonyl groups: one aldehyde (-CHO), one ester (-COOCH3), and one ketone (-C=O).
Step 2: Understand the reactivity of NaBH4. Sodium borohydride (NaBH4) is a reducing agent that selectively reduces aldehydes and ketones to their corresponding alcohols but does not typically reduce esters under standard conditions.
Step 3: Predict the reduction of the aldehyde group. The aldehyde group (-CHO) will be reduced to a primary alcohol (-CH2OH) by NaBH4 in methanol.
Step 4: Predict the reduction of the ketone group. The ketone group (-C=O) will be reduced to a secondary alcohol (-CH(OH)-) by NaBH4 in methanol.
Step 5: Note that the ester group (-COOCH3) will remain unchanged because NaBH4 does not reduce esters under these conditions. The final product will have a primary alcohol, a secondary alcohol, and an intact ester group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Sodium Borohydride (NaBH4) as a Reducing Agent
Sodium borohydride (NaBH4) is a mild 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 electrophilic carbon of the carbonyl group, facilitating the reduction process. Understanding its reactivity and selectivity is crucial for predicting the products of reactions involving NaBH4.
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09:28
Reducing Agents
Mechanism of Reduction
The reduction mechanism typically involves the nucleophilic attack of the hydride ion on the carbonyl carbon, followed by protonation of the resulting alkoxide intermediate. This stepwise process leads to the formation of alcohols. Familiarity with this mechanism helps in visualizing how different functional groups will react with NaBH4 and what products will be formed.
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04:40Birch Reduction Mechanism
Solvent Effects in Organic Reactions
The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves as a polar protic solvent that can stabilize charged intermediates and facilitate proton transfer. Understanding the role of the solvent is essential for predicting reaction pathways and product distributions, especially in reduction reactions where solvation can affect reactivity.
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02:26General format of reactions and how to interpret solvents.
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
1647
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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
1704
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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)
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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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.
(a) CH3–(CH2)8–CHO
1607
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