Domanda del libro di testo
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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TOC.tableOfContents
- 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
Capitolo 23, Problema 52k
Predict the products obtained when D-galactose reacts with each reagent.
(k) excess HIO4
Guida verificata passo dopo passo1
Understand the reaction: Periodic acid (HIO4) is an oxidizing agent that cleaves vicinal diols (two hydroxyl groups on adjacent carbons) in carbohydrates. It breaks the C-C bond between the carbons bearing the hydroxyl groups, forming smaller carbonyl-containing fragments such as aldehydes or formic acid.
Analyze the structure of D-galactose: D-galactose is an aldohexose, meaning it has six carbons, with an aldehyde group at C1 and hydroxyl groups on the other carbons. Draw the Fischer projection of D-galactose to visualize the vicinal diols.
Identify the vicinal diols: In D-galactose, vicinal diols are present between C2-C3, C3-C4, C4-C5, and C5-C6. These are the sites where HIO4 will cleave the C-C bonds.
Determine the cleavage products: For each vicinal diol, the C-C bond is broken, and each carbon forms a carbonyl group. Depending on the position of the carbon, the products will be either formaldehyde (HCHO), formic acid (HCOOH), or a larger aldehyde/ketone.
Combine the results: After cleaving all vicinal diols in excess HIO4, the D-galactose molecule will be completely broken down into smaller fragments. Write out the specific products formed from each cleavage site to complete the reaction analysis.
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Concetti chiave
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D-Galactose Structure
D-galactose is a six-carbon aldose sugar with a specific stereochemistry. It contains an aldehyde group at one end and multiple hydroxyl groups, which influence its reactivity. Understanding its structure is crucial for predicting how it will react with various reagents, including oxidative agents like HIO4.
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Monosaccharides - D and L Isomerism
Periodic Acid Oxidation
Periodic acid (HIO4) is a strong oxidizing agent that cleaves vicinal diols and aldehydes. In the case of sugars, it can oxidatively cleave the carbon-carbon bonds adjacent to hydroxyl groups, leading to the formation of smaller aldehydes or ketones. This reaction is essential for understanding the products formed when d-galactose is treated with excess HIO4.
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04:15Monosaccharides - Weak Oxidation (Aldonic Acid)
Reaction Mechanism
The reaction mechanism describes the step-by-step process by which reactants are converted into products. For d-galactose reacting with HIO4, the mechanism involves the formation of cyclic intermediates and subsequent cleavage of the sugar backbone. A clear grasp of these mechanisms helps in predicting the final products of the reaction.
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02:16Heck Reaction Mechanism
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Predict the products obtained when D-galactose reacts with each reagent.
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