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 42b

Textbook Question

Convert the line-angle drawings into Fischer projections.
(b)

Verified step by step guidance

Step 1: Identify the chiral centers in the line-angle drawing. Chiral centers are carbon atoms bonded to four different groups. Ensure you recognize the stereochemistry (R or S configuration) at each chiral center.

Step 2: Orient the molecule so that the longest carbon chain is vertical, with the most oxidized carbon (e.g., a carbonyl or carboxylic group) at the top. This orientation is essential for constructing a Fischer projection.

Step 3: Determine the spatial arrangement of substituents around each chiral center. In a Fischer projection, horizontal lines represent bonds coming out of the plane (toward the viewer), and vertical lines represent bonds going into the plane (away from the viewer).

Step 4: Translate the 3D structure into a 2D Fischer projection by placing the substituents appropriately. Ensure that the stereochemistry (R or S) is preserved during this conversion. Double-check the configuration by assigning priorities to the substituents and using the Cahn-Ingold-Prelog rules.

Step 5: Verify the Fischer projection by mentally converting it back into a 3D structure and comparing it to the original line-angle drawing. Ensure that the stereochemistry and connectivity are consistent between the two representations.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Line-Angle Drawings

Line-angle drawings, also known as skeletal structures, are a simplified way of representing organic molecules. In these drawings, carbon atoms are represented by the ends and intersections of lines, while hydrogen atoms are often omitted for clarity. This method allows chemists to visualize complex structures quickly, focusing on the connectivity of atoms rather than their individual bonds.

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In this format, the vertical lines represent bonds that are oriented away from the viewer, while horizontal lines indicate bonds that are coming towards the viewer. Fischer projections are especially important for illustrating the configuration of chiral centers in carbohydrates and amino acids.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is crucial for understanding isomerism, where compounds with the same molecular formula can have different structures and properties. In the context of converting line-angle drawings to Fischer projections, recognizing the stereochemical configuration of chiral centers is essential to accurately represent the molecule's 3D orientation.

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