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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3:12 minutes

Problem 42c

Textbook Question

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

Verified step by step guidance

Analyze the given line-angle drawing to identify the carbon chain and the substituents attached to each carbon. Note the stereochemistry (wedges and dashes) to determine the 3D configuration of the molecule.

Determine the longest continuous carbon chain in the molecule and label the carbons sequentially, starting from one end. This will help in organizing the structure for the Fischer projection.

Orient the molecule so that the main carbon chain is vertical, with the most oxidized carbon (e.g., a carbonyl or hydroxyl group) at the top. Ensure that horizontal bonds point toward the viewer (out of the plane) and vertical bonds point away (into the plane).

Translate the 3D configuration into a 2D Fischer projection by placing the substituents on the horizontal and vertical lines. Use the stereochemical information (R/S configuration or wedges/dashes) to ensure the correct placement of groups.

Double-check the Fischer projection to confirm that it accurately represents the stereochemistry and connectivity of the original line-angle drawing.

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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 shorthand representation of organic molecules where lines represent bonds between atoms. Each vertex or endpoint of a line corresponds to a carbon atom, and hydrogen atoms are typically omitted for clarity. This method simplifies the visualization of complex structures, making it easier to identify functional groups and molecular geometry.

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In a Fischer projection, the vertical lines represent bonds that are oriented away from the viewer, while horizontal lines represent bonds that are coming towards the viewer. This format is 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 Fischer projections, recognizing the stereochemical configuration of chiral centers is essential for accurately converting line-angle drawings to Fischer representations.

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Related Practice

Textbook Question

For each Fischer projection,

1. make a model.

2. draw the mirror

3.. determine whether the mirror is the same as, or different from, the original structure.

4. draw any mirror planes of symmetry that are apparent from the Fischer projections.

(c)

(d)

Textbook Question

For each set of examples, make a model of the first structure, and indicate the relationship of each of the other structures to the first structure. Examples of relationships: same compound, enantiomer, structural isomer.

(a)

Textbook Question

Convert the following Fischer projections to perspective formulas.

(a)

(b)

Textbook Question

Convert the line-angle drawings into Fischer projections.

(b)

Textbook Question

Convert the line-angle drawings into Fischer projections.

(a)

Textbook Question

Draw Fischer projections of the following molecules.

(a)

Textbook Question

Draw Fischer projections of the following molecules.

(b)

Textbook Question

In this attempt to convert the line angle drawing of d-erythrose (shown) to the Fischer projection (shown), by viewing it from a certain direction (shown), a mistake was made. What was the mistake?

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

Key Concepts

Line-Angle Drawings

Fischer Projections

Stereochemistry

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