Domanda del libro di testo
Look at the open-chain form of D-mannose and draw the two glycosidic products that you expect to obtain by reacting D-mannose with methanol.
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Ch.20 Carbohydrates
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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TOC.tableOfContents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Capitolo 20, Problema 53
Reduction of D-fructose with a reducing agent yields a mixture of D-sorbitol along with a second, isomeric product. What is the structure of the second product?
Guida verificata passo dopo passo1
Understand the context: Reduction of D-fructose involves the addition of hydrogen (H₂) to the carbonyl group (C=O) in the sugar molecule, converting it into an alcohol group (-OH). This process is typically carried out using a reducing agent such as sodium borohydride (NaBH₄) or hydrogen gas with a catalyst.
Identify the structure of D-fructose: D-fructose is a ketohexose, meaning it contains six carbons and a ketone group at the second carbon (C2). The ketone group is the functional group that will be reduced.
Determine the products of reduction: Reduction of the ketone group in D-fructose can yield two different products because the ketone group is located at C2, which is adjacent to a chiral center (C3). Reduction can produce either D-sorbitol (a sugar alcohol derived from D-glucose) or another isomeric sugar alcohol.
Explain the formation of the second product: The second product is D-mannitol, which forms when the reduction of the ketone group leads to the formation of a hydroxyl group (-OH) with the opposite stereochemistry at C2 compared to D-sorbitol. This occurs because the reduction process can produce a racemic mixture at the C2 position.
Summarize the structures: The two products of the reduction of D-fructose are D-sorbitol (with the same stereochemistry as D-glucose) and D-mannitol (with the stereochemistry of D-mannose). Both are sugar alcohols, differing only in the configuration of the hydroxyl group at C2.
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Reduction of Sugars
Reduction of sugars involves the conversion of carbonyl groups (aldehydes or ketones) into alcohols using reducing agents. In the case of d-fructose, a ketose sugar, reduction leads to the formation of d-sorbitol, an alditol. Understanding this process is crucial for predicting the products of sugar reduction.
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Percorso guidato
0:50
Reduction of Monosaccharides Concept 1
Isomerism
Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements or spatial orientations. In the context of d-fructose reduction, the second product formed alongside d-sorbitol is likely to be an isomer, such as d-mannitol, which has a different configuration at one or more carbon atoms.
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Percorso guidato
1:26Glycolysis Concept 5
Structural Representation of Sugars
Structural representation of sugars involves depicting their molecular structure, including the arrangement of atoms and functional groups. For d-fructose and its reduction products, understanding how to draw and interpret Fischer projections or Haworth structures is essential for identifying the second product's structure and its relationship to d-sorbitol.
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2:08Molecular Representations Concept 1
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Domanda del libro di testo
Oxidation of the aldehyde group of ribose yields a carboxylic acid. Draw the structure of ribonic acid.
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Domanda del libro di testo
In its open-chain form, D-mannose, an aldohexose found in orange peels, has the structure shown here. Coil mannose around and draw it in the cyclic hemiacetal ⍺ and β forms.
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Domanda del libro di testo
Treatment of D-glucose with a reducing agent yields sorbitol, a substance used as a sugar substitute by people with diabetes. Draw the structure of sorbitol.
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Domanda del libro di testo
Treatment of an aldose with an oxidizing agent such as Tollens’ reagent yields a carboxylic acid. Gluconic acid, the product of glucose oxidation, is used as its magnesium salt for the treatment of magnesium deficiency. Draw the structure of gluconic acid.
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Domanda del libro di testo
Sucrose and D-glucose rotate plane-polarized light to the right; D-fructose rotates light to the left. When sucrose is hydrolyzed, the glucose–fructose mixture rotates light to the left.
b. Why do you think the mixture is called “invert sugar”?
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