Domanda del libro di testo
How are the following pairs of carbohydrates, shown in a Fischer projection, related to each other? Are they structural isomers, enantiomers, diastereomers, or epimers? Identify each as the D- or L-isomer.
(a)
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Ch.6 Carbohydrates Life's Sweet Molecules
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696
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TOC.tableOfContents
- Ch.4 Introduction to Organic Compounds75
- Ch.5 Chemical Reactions19
- Ch.6 Carbohydrates Life's Sweet Molecules62
- Ch.7 States of Matter and Their Attractive Forces8
- Ch.8 Solution Chemistry Sugar and Water Do Mix4
- Ch.10 Proteins Workers of the Cell89
- Ch.11 Nucleic Acids Big Molecules with a Big Role69
- Ch.12 Food as Fuel An Overview of Metabolism65
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Non è quello che usi tu?Cambia libro di testo
Capitolo 3, Problema 65
Draw the Fischer projection of the C3 epimer of D-glucose. Compare your structure with those in Table 6.1 and give the name of this compound.
Guida verificata passo dopo passo1
Understand the concept of epimers: Epimers are stereoisomers that differ in configuration at only one chiral center. In this case, the C3 epimer of D-glucose means the configuration at the third carbon atom will be inverted compared to D-glucose.
Review the Fischer projection of D-glucose: D-glucose is a six-carbon aldose with the following configuration in its Fischer projection: the hydroxyl groups (-OH) on C2, C4, and C5 are on the right side, while the hydroxyl group on C3 is on the left side.
Invert the configuration at C3: To create the C3 epimer, change the position of the hydroxyl group at the third carbon. In the Fischer projection, move the hydroxyl group from the left side to the right side at C3, while keeping the configurations at all other chiral centers unchanged.
Compare the resulting structure with Table 6.1: After modifying the Fischer projection, compare the new structure to the compounds listed in Table 6.1 to identify the name of the C3 epimer of D-glucose.
Name the compound: Based on the comparison, the C3 epimer of D-glucose is identified as D-allose. Ensure the name matches the structure derived from the inversion at C3.
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Fischer Projection
The Fischer projection is a two-dimensional representation of a three-dimensional organic molecule, particularly useful for depicting carbohydrates. In this format, the vertical lines represent bonds that are oriented away from the viewer, while horizontal lines represent bonds that are coming towards the viewer. This method simplifies the visualization of stereochemistry, allowing for easy identification of chiral centers and their configurations.
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Percorso guidato
0:48
Fischer Projections Example 1
C3 Epimer
C3 epimers are a specific type of diastereomer that differ in configuration at only one chiral center, in this case, the third carbon atom of the sugar molecule. For d-glucose, the C3 epimer is d-mannose, which has a different spatial arrangement of atoms at the third carbon. Understanding epimerization is crucial for distinguishing between similar sugars and their biological roles.
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1:26D vs L Enantiomers Example 2
D-Glucose
D-glucose is a simple sugar and an important carbohydrate in biology, serving as a primary energy source for cells. It is a six-carbon aldose with the molecular formula C6H12O6 and exists in various forms, including linear and cyclic structures. Recognizing its structure and derivatives, such as epimers, is essential for understanding carbohydrate chemistry and metabolism.
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2:48Total Energy From Glucose Concept 2
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