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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3:23 minutes

Problem 59

Textbook Question

Convert the Fischer projection to a perspective formula.

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 coming out of the plane (towards the viewer) and vertical lines represent bonds going behind the plane (away from the viewer).

Step 2: Identify the groups attached to the central carbon atom in the Fischer projection. In this case, the groups are CH3 (top), CH3 (bottom), HO (left), and Br (right). The two hydrogens are also present on the vertical axis.

Step 3: Convert the horizontal bonds (HO and Br) into wedges in the perspective formula. These groups are coming out of the plane towards the viewer, so they should be represented as solid wedges in the perspective formula.

Step 4: Convert the vertical bonds (CH3 groups) into dashed lines in the perspective formula. These groups are going behind the plane away from the viewer, so they should be represented as dashed lines in the perspective formula.

Step 5: Arrange the groups in the perspective formula to maintain the stereochemistry of the molecule. Ensure that the spatial arrangement of the groups matches the original Fischer projection, preserving the correct configuration of the molecule.

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Key Concepts

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

Fischer Projection

A Fischer projection is a two-dimensional representation of a molecule, typically used for carbohydrates and amino acids, where the vertical lines represent bonds going back into the plane and the horizontal lines represent bonds coming out of the plane. This format helps visualize the stereochemistry of chiral centers, allowing for easy identification of the configuration (D or L) of sugars and amino acids.

Perspective Formula

A perspective formula, often depicted in three dimensions, illustrates the spatial arrangement of atoms in a molecule. This representation emphasizes the three-dimensional orientation of bonds and groups, making it easier to understand molecular geometry and interactions. It is particularly useful for visualizing how molecules might interact in chemical reactions.

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 due to the orientation of their atoms. Mastery of stereochemistry is essential for converting between different molecular representations, such as Fischer projections and perspective formulas.

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Related Practice

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)

Textbook Question

Convert the following Fischer projections to perspective formulas.

(a)

(b)

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