Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

5. Chirality

Fischer Projection

Organic Chemistry

5. Chirality

Fischer Projection

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6:31 minutes

Problem 28a,b

Textbook Question

Convert the following perspective formulas to Fischer projections.
(a)
(b)

Verified step by step guidance

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.

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.

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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