Textbook Question
Identify each of the following as D or L:
a.
Ch.13 Carbohydrates
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353
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Table of contents
- Ch.1 Chemistry in Our Lives11
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy54
- Ch.4 Atoms and Elements51
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions41
- Ch.8 Gases29
- Ch.9 Solutions51
- Ch.10 Acids and Bases and Equilibrium65
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons78
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones83
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides90
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis83
- Ch.18 Metabolic Pathways and ATP Production67
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 13, Problem 23c,d
Draw the Fischer projection for the other enantiomer of c to d in problem 13.21.
c. 
d. 
Verified step by step guidance1
Understand the concept of a Fischer projection: A Fischer projection is a two-dimensional representation of a molecule, where the vertical lines represent bonds going into the plane (away from the viewer) and the horizontal lines represent bonds coming out of the plane (toward the viewer). The carbon chain is typically drawn vertically, with the most oxidized carbon at the top.
Identify the chiral center(s) in the molecule: A chiral center is a carbon atom bonded to four different groups. Locate the chiral center(s) in the given molecule (c to d in problem 13.21).
Determine the configuration of the given enantiomer: Analyze the spatial arrangement of the groups around the chiral center in the provided Fischer projection. Assign the configuration as R or S using the Cahn-Ingold-Prelog priority rules.
Invert the configuration to find the other enantiomer: To draw the Fischer projection of the other enantiomer, swap the positions of the groups on the horizontal bonds (left and right) while keeping the vertical bonds (top and bottom) unchanged. This inversion changes the configuration at the chiral center.
Redraw the Fischer projection: Carefully redraw the molecule with the inverted configuration, ensuring that the vertical and horizontal bonds are correctly represented. Verify that the new Fischer projection corresponds to the enantiomer of the original molecule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Fischer Projection
A Fischer projection is a two-dimensional representation of a three-dimensional organic molecule, particularly useful for depicting stereochemistry. In this format, vertical lines represent bonds that project away from the viewer, while horizontal lines indicate bonds that come towards the viewer. This method is commonly used for carbohydrates and amino acids to illustrate their stereoisomers.
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Fischer Projections Example 1
Enantiomers
Enantiomers are a type of stereoisomer that are non-superimposable mirror images of each other. They typically arise in molecules that contain one or more chiral centers, where the arrangement of atoms around the chiral center leads to two distinct configurations. Understanding enantiomers is crucial in fields like pharmacology, as different enantiomers can have vastly different biological effects.
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Chirality
Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image, akin to how left and right hands are mirror images but cannot be perfectly aligned. A chiral molecule usually contains at least one carbon atom bonded to four different substituents, creating two distinct configurations. Recognizing chirality is essential for predicting the behavior of molecules in biological systems and chemical reactions.
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Related Practice
Textbook Question
Identify each of the following as the D or L enantiomer:
a.
Textbook Question
Draw the Fischer projection for the other enantiomer of a to b in problem 13.21.
a.
b.
Textbook Question
Draw the Fischer projections for D-glucose and L-glucose.
1
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Textbook Question
An infant with galactosemia can utilize D-glucose in milk but not d-galactose. How does the Fischer projection of D-galactose differ from that of D-glucose?
Textbook Question
D-Fructose is the sweetest monosaccharide. How does the Fischer projection of D-fructose differ from that of D-glucose?