Textbook Question
What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?
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 25b
Show what happens when the product of part (a) is hydrolyzed using dilute acid.
Verified step by step guidance1
Identify the product from part (a) and determine its functional groups. For example, if the product contains an ester group, hydrolysis will target this functional group.
Understand the mechanism of acid-catalyzed hydrolysis. In this reaction, the ester group reacts with water in the presence of a dilute acid (e.g., HCl or H2SO4) to form a carboxylic acid and an alcohol.
Write the general reaction for acid-catalyzed hydrolysis: , where R represents alkyl or aryl groups.
Propose the specific hydrolysis reaction for the product of part (a). Replace the generic R groups in the general reaction with the actual groups from the product of part (a).
Draw the structures of the resulting products (e.g., the carboxylic acid and alcohol) and ensure that the reaction is balanced. Verify that the hydrolysis mechanism is consistent with the functional groups present in the product of part (a).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrolysis
Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In organic chemistry, it often refers to the reaction of a compound with water or an aqueous solution, leading to the formation of new products. When hydrolyzing an organic compound, such as an ester or an amide, the reaction typically results in the formation of an alcohol and a carboxylic acid or an amine, respectively.
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Dilute Acid
A dilute acid is an acid that has been mixed with a significant amount of water, reducing its concentration. In hydrolysis reactions, dilute acids, such as hydrochloric acid (HCl) or sulfuric acid (H2SO4), are often used as catalysts to facilitate the reaction. The presence of a dilute acid can help to protonate the reactants, making them more reactive and promoting the cleavage of bonds during hydrolysis.
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Reaction Mechanism
A reaction mechanism is a step-by-step description of the process by which reactants are converted into products in a chemical reaction. Understanding the mechanism of hydrolysis is crucial, as it involves several stages, including protonation of the substrate, nucleophilic attack by water, and subsequent bond cleavage. This knowledge helps predict the products formed and the conditions required for the reaction to proceed efficiently.
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Related Practice
Textbook Question
Propose a mechanism for methylation of any one of the hydroxy groups of methyl α-D-glucopyranoside, using NaOH and dimethyl sulfate.
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Textbook Question
Show the products that result from hydrolysis of amygdalin in dilute acid. Can you suggest why amygdalin might be toxic to tumor (and possibly other) cells?
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Textbook Question
Draw the expected product of the reaction of the following sugars with excess methyl iodide and silver oxide.
(a) α-D-fructofuranose
Textbook Question
Treatment of either anomer of fructose with excess ethanol in the presence of a trace of HCl gives a mixture of the α and β anomers of ethyl-D-fructofuranoside. Draw the starting materials, reagents, and products for this reaction. Circle the aglycone in each product.
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Textbook Question
Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.