Textbook Question
For each pair, give the relationship between the two compounds. Making models will be helpful.
(g)
5. Chirality
Fischer Projection
6:31 minutesProblem 28a,b
Textbook Question
Convert the following perspective formulas to Fischer projections.
(a) 
(b) 
Verified step by step guidance1
Step 1: Understand the perspective formula. The perspective formula uses wedge and dash bonds to represent the 3D spatial arrangement of substituents around a chiral center. Wedge bonds indicate groups coming out of the plane towards the viewer, while dash bonds indicate groups going behind the plane.
Step 2: Identify the chiral center and substituents. For molecule A, the chiral center is the carbon atom bonded to F, OH, Br, and CH3. For molecule B, the chiral center is the carbon atom bonded to Cl, OH, F, and CH3.
Step 3: Assign priorities to the substituents based on the Cahn-Ingold-Prelog rules. Higher atomic numbers get higher priority. For molecule A, the priorities are: F > Br > OH > CH3. For molecule B, the priorities are: Cl > F > OH > CH3.
Step 4: Orient the molecule so that the lowest priority group (CH3 for A, CH3 for B) is pointing away from the viewer (on the dashed bond). This orientation is crucial for correctly converting to a Fischer projection.
Step 5: Draw the Fischer projection. In a Fischer projection, the horizontal bonds represent groups coming out of the plane, and the vertical bonds represent groups going behind the plane. Arrange the substituents accordingly based on the orientation determined in Step 4.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Fischer Projections
Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In these projections, vertical lines represent bonds that extend away from the viewer, while horizontal lines represent bonds that come towards the viewer. This format is especially important for visualizing the configuration of chiral centers in carbohydrates and amino acids.
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Chirality
Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. Molecules with chirality typically have one or more chiral centers, usually carbon atoms bonded to four different substituents. Understanding chirality is crucial for converting perspective formulas to Fischer projections, as the spatial arrangement of groups around the chiral center determines the molecule's stereochemistry.
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Perspective Formulas
Perspective formulas are three-dimensional representations of molecules that illustrate the spatial arrangement of atoms and bonds. They often use wedge and dashed lines to indicate bonds that are oriented towards or away from the viewer. Converting these perspective formulas to Fischer projections requires careful attention to the orientation of substituents to accurately reflect the molecule's stereochemistry in a two-dimensional format.
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