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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5:04 minutes

Problem 42a

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the line-angle drawing provided. The molecule is a carbon chain with two chlorine atoms attached to the central carbon. The wedge and dash bonds indicate stereochemistry, where the wedge bond represents a group coming out of the plane (towards the viewer) and the dash bond represents a group going behind the plane (away from the viewer).

Step 2: Identify the substituents on the central carbon atom. The central carbon is bonded to a chlorine atom (on the wedge), another chlorine atom (on the dash), a methyl group (CH₃), and another methyl group (CH₃).

Step 3: Orient the molecule to prepare for conversion into a Fischer projection. In a Fischer projection, the horizontal bonds represent groups coming out of the plane, and the vertical bonds represent groups going behind the plane. Rotate the molecule mentally or on paper to align it with this convention.

Step 4: Assign the substituents to the appropriate positions in the Fischer projection. Place the chlorine atoms on the horizontal axis (since they are on the wedge and dash bonds), and place the methyl groups on the vertical axis (since they are in the plane of the paper).

Step 5: Draw the Fischer projection. The central carbon is represented as a cross, with the chlorine atoms on the left and right (horizontal axis) and the methyl groups on the top and bottom (vertical axis). Ensure the stereochemistry is preserved by correctly assigning the wedge and dash bonds to the horizontal axis.

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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 vertices represent carbon atoms and lines represent bonds. This method simplifies the depiction of complex molecules by omitting hydrogen atoms attached to carbons, making it easier to visualize the overall structure and connectivity of the molecule.

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In this format, the vertical lines represent bonds that are oriented away from the viewer, while horizontal lines represent bonds that are coming towards the viewer. This projection 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. Understanding stereochemistry is crucial when converting between line-angle drawings and Fischer projections, as it involves recognizing the orientation of substituents around chiral centers. Properly representing stereochemistry ensures accurate communication of molecular structure and reactivity.

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