Textbook Question
Predict the products obtained when D-galactose reacts with each reagent.
(h) NaBH4
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Ch. 23 - Carbohydrates and Nucleic Acids
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 23, Problem 52i
Predict the products obtained when D-galactose reacts with each reagent.
(i) Br2, H2O, then H2O2 and Fe2(SO4)3
Verified step by step guidance1
Step 1: Understand the structure of D-galactose. D-galactose is an aldohexose, meaning it contains six carbon atoms and an aldehyde functional group at the first carbon. The hydroxyl groups are arranged in a specific stereochemistry along the carbon chain.
Step 2: Analyze the reaction with Br₂ in H₂O. Bromine in water selectively oxidizes the aldehyde group (-CHO) at the first carbon of D-galactose to a carboxylic acid group (-COOH), forming D-galactonic acid. This reaction does not affect the hydroxyl groups or the stereochemistry of the sugar.
Step 3: Consider the subsequent reaction with H₂O₂ and Fe₂(SO₄)₃. This combination of reagents is a strong oxidizing system. It further oxidizes the primary alcohol group (-CH₂OH) at the sixth carbon of D-galactonic acid to a carboxylic acid group (-COOH), resulting in the formation of D-galactaric acid (also known as mucic acid).
Step 4: Summarize the transformations. The aldehyde group at C-1 is oxidized to a carboxylic acid in the first step, and the primary alcohol group at C-6 is oxidized to a carboxylic acid in the second step. The final product is a dicarboxylic acid, D-galactaric acid.
Step 5: Verify the stereochemistry. Throughout the reaction, the stereochemistry of the hydroxyl groups on carbons 2, 3, 4, and 5 remains unchanged, as the oxidation reactions are specific to the aldehyde and primary alcohol groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
D-Galactose Structure
D-galactose is a six-carbon aldose sugar with a specific stereochemistry. It contains an aldehyde functional group and multiple hydroxyl groups, which are crucial for its reactivity. Understanding its structure helps predict how it will interact with reagents, particularly in oxidation and substitution reactions.
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Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the conversion of alcohols to carbonyl compounds. In the context of D-galactose, reagents like Br2 and H2O can oxidize the aldehyde group, leading to the formation of carboxylic acids or other oxidized products, which is essential for predicting the reaction outcomes.
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Radical Mechanisms
Radical mechanisms involve the formation of reactive species with unpaired electrons, which can initiate further reactions. In the presence of H2O2 and Fe2(SO4)3, radicals may be generated that can react with the oxidized products of D-galactose, leading to various secondary reactions. Understanding these mechanisms is key to predicting the final products of the reaction sequence.
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Related Practice
Textbook Question
Predict the products obtained when D-galactose reacts with each reagent.
(k) excess HIO4
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Textbook Question
Predict the products obtained when d-galactose reacts with each reagent.
(f) excess Ac2O and pyridine
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Textbook Question
Draw the following sugar derivatives.
(a) methyl β-D-glucopyranoside
(b) 2,3,4,6-tetra-O-methyl-D-mannopyranose
(c) 1,3,6-tri-O-methyl-D-fructofuranose
(d) methyl 2,3,4,6-tetra-O-methyl-β-D-galactopyranoside
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Textbook Question
Predict the products obtained when d-galactose reacts with each reagent.
(g) excess CH3I, Ag2O
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Textbook Question
Predict the products obtained when D-galactose reacts with each reagent.
(j) (1) KCN/HCN; (2) H2, Pd/BaSO4; (3) H3O+
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