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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2:37 minutes

Problem 28c,d

Textbook Question

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

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 atoms around a chiral center. Wedge bonds indicate atoms coming out of the plane towards the viewer, while dash bonds indicate atoms going behind the plane.

Step 2: Identify the chiral centers in the molecule. For both structures, locate the carbon atoms that are bonded to four different groups. These are the chiral centers.

Step 3: Assign the groups around each chiral center to their respective positions in a Fischer projection. In a Fischer projection, the horizontal bonds represent groups coming out of the plane (towards the viewer), and the vertical bonds represent groups going behind the plane.

Step 4: Rotate the molecule mentally or on paper to align the groups correctly for the Fischer projection. Ensure that the groups on the horizontal axis are the ones coming out of the plane, and the groups on the vertical axis are the ones going behind the plane.

Step 5: Draw the Fischer projection. Place the chiral centers vertically, with the substituents arranged according to the spatial orientation determined in the previous step. Ensure that the stereochemistry (R or S configuration) is preserved during the conversion.

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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 helpful for visualizing chiral centers and understanding the spatial arrangement of substituents around them.

Chirality

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral molecule typically has at least one carbon atom bonded to four different substituents, creating two distinct stereoisomers. Understanding chirality is crucial for predicting the behavior of molecules in biological systems, as different enantiomers can have vastly different effects.

Substituent Prioritization

In converting perspective formulas to Fischer projections, it is essential to prioritize substituents based on the Cahn-Ingold-Prelog (CIP) rules. These rules dictate that substituents are ranked according to atomic number, with higher atomic numbers receiving higher priority. This prioritization is vital for accurately determining the configuration (R or S) of chiral centers and ensuring correct representation in Fischer projections.

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Related Practice

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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Textbook Question

Draw Fischer projections of the following molecules.

(c)

Textbook Question

Convert the following Fischer projections to perspective formulas

(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)

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

Key Concepts

Fischer Projections

Chirality

Substituent Prioritization

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