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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6:09 minutes

Problem 29c,d

Textbook Question

Convert the following Fischer projections to perspective formulas
(c)
(d)

Verified step by step guidance

Step 1: Understand the Fischer projection. A Fischer projection is a 2D representation of a molecule where horizontal lines represent bonds projecting out of the plane (towards the viewer) and vertical lines represent bonds projecting into the plane (away from the viewer).

Step 2: Identify the substituents on the central carbon atom in the Fischer projection. For image (c), the substituents are CH₂OH (top), CH₃ (bottom), Br (left), and Cl (right). For image (d), the substituents are CH₂OH (top), CH₃ (bottom), H (left and right), Br (middle left), and Cl (middle right).

Step 3: Convert the Fischer projection to a perspective formula. In a perspective formula, the central carbon atom is represented in 3D, with wedge bonds (solid triangle) indicating substituents coming out of the plane towards the viewer and dashed bonds (dashed triangle) indicating substituents going into the plane away from the viewer.

Step 4: Assign the correct spatial arrangement of substituents. For image (c), place CH₂OH and CH₃ on the vertical axis (into and out of the plane), and Br and Cl on the horizontal axis (towards and away from the viewer). For image (d), place CH₂OH and CH₃ on the vertical axis, and H, Br, and Cl on the horizontal axis with appropriate stereochemistry.

Step 5: Draw the perspective formula. Use wedge and dashed bonds to represent the spatial arrangement of substituents based on the Fischer projection. Ensure that the stereochemistry is preserved during the conversion process.

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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 organic molecules, particularly carbohydrates, that depict the stereochemistry of chiral centers. In these projections, vertical lines represent bonds that extend away from the viewer, while horizontal lines represent bonds that come towards the viewer. Understanding Fischer projections is essential for converting them into three-dimensional perspective formulas.

Perspective Formulas

Perspective formulas illustrate the three-dimensional arrangement of atoms in a molecule, showing how the atoms are oriented in space. These formulas use wedge and dash notation, where solid wedges indicate bonds that project out of the plane towards the viewer, and dashed lines indicate bonds that extend behind the plane. Converting Fischer projections to perspective formulas requires a clear understanding of these spatial representations.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this arrangement affects their chemical properties and reactions. It is crucial for understanding isomerism, particularly in chiral molecules, where different spatial configurations can lead to different biological activities. Recognizing the stereochemical implications of a molecule is vital when converting between different representations like Fischer projections and perspective formulas.

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Related Practice

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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Textbook Question

Draw Fischer projections of the following molecules.

(c)

Textbook Question

Convert the following perspective formulas to Fischer projections.

(c)

(d)

Textbook Question

(a) There is only one ketotriose, called dihydroxyacetone. Draw its structure.

(b) There is only one aldotriose, called glyceraldehyde. Draw the two enantiomers of glyceraldehyde.

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.

(c)

Textbook Question

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(e) (R,R)-2,3-dibromobutane

(f)

Textbook Question

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.

(e)

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Convert the following Fischer projections to perspective formulas(c) (d)

Key Concepts

Fischer Projections

Perspective Formulas

Stereochemistry

Watch next

Convert the following Fischer projections to perspective formulas
(c)
(d)