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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2:35 minutes

Problem 27

Textbook Question

Convert the Fischer projection to a perspective formula.

Verified step by step guidance

Step 1: Understand the Fischer projection. The Fischer projection is a two-dimensional representation of a molecule where horizontal lines represent bonds projecting out of the plane (toward the viewer), and vertical lines represent bonds projecting behind the plane (away from the viewer). The central cross represents the chiral carbon.

Step 2: Identify the substituents on the chiral carbon. In the given Fischer projection, the substituents are: COO⁻ (carboxylate group) at the top, H (hydrogen) on the left, CH₃ (methyl group) on the right, and CH₂CH₃ (ethyl group) at the bottom.

Step 3: Assign the spatial orientation of the substituents. In the Fischer projection, the horizontal substituents (H and CH₃) are coming out of the plane toward the viewer, while the vertical substituents (COO⁻ and CH₂CH₃) are going behind the plane away from the viewer.

Step 4: Draw the perspective formula. To convert to a perspective formula, place the chiral carbon at the center. Represent the horizontal substituents (H and CH₃) as wedges (solid triangular bonds) pointing toward the viewer, and the vertical substituents (COO⁻ and CH₂CH₃) as dashed lines (dashed triangular bonds) pointing away from the viewer.

Step 5: Double-check the stereochemistry. Ensure that the spatial arrangement of the substituents in the perspective formula matches the original Fischer projection. Verify that the substituents are correctly oriented relative to the chiral carbon.

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Key Concepts

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

Fischer Projection

The Fischer projection is a two-dimensional representation of a molecule, particularly useful for depicting the stereochemistry of carbohydrates and amino acids. In this format, vertical lines represent bonds that project away from the viewer, while horizontal lines indicate bonds that come towards the viewer. Understanding how to interpret Fischer projections is essential for converting them into three-dimensional representations.

Perspective Formula

A perspective formula, often depicted in a three-dimensional format, illustrates the spatial arrangement of atoms in a molecule. This representation helps visualize the actual geometry of the molecule, including bond angles and the orientation of substituents. Converting from Fischer projections to perspective formulas requires an understanding of how to translate the two-dimensional layout into a three-dimensional context.

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, where compounds with the same molecular formula can have different structures and properties. Knowledge of stereochemistry is vital when converting Fischer projections to perspective formulas, as it ensures the correct orientation of substituents in three-dimensional space.

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Related Practice

Textbook Question

Give the stereochemical relationships between each pair of structures. Examples are same compound, structural isomers, enantiomers, and diastereomers. Which pairs could you (theoretically) separate by distillation or recrystallization?

(a)

(b)

Textbook Question

Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?

Textbook Question

For each pair, give the relationship between the two compounds. Making models will be helpful.

(g)

Multiple Choice

Draw the following aldotetrose in the proper Fischer projection.

Textbook Question

Convert the Fischer projection to a perspective formula.

Textbook Question

Convert the following perspective formulas to Fischer projections.

(a)

(b)

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)

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