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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2:58 minutes

Problem 7c

Textbook Question

Draw Fischer projections of the following molecules.
(c)

Verified step by step guidance

Step 1: Understand the structure provided. The molecule has an amine group (NH₂) attached to a chiral carbon, along with a phenyl group (Ph) and a methyl group (CH₃). The dashed wedge indicates that the NH₂ group is oriented away from the viewer.

Step 2: Recall the rules for drawing Fischer projections. In a Fischer projection, the horizontal lines represent bonds coming out of the plane (towards the viewer), and the vertical lines represent bonds going into the plane (away from the viewer). The chiral carbon is at the intersection of the lines.

Step 3: Assign priorities to the substituents based on the Cahn-Ingold-Prelog rules. The NH₂ group has the highest priority, followed by the phenyl group (Ph), the methyl group (CH₃), and finally the hydrogen atom.

Step 4: Orient the molecule so that the lowest priority group (hydrogen) is on the vertical line pointing away from the viewer. This ensures the correct stereochemistry is represented in the Fischer projection.

Step 5: Draw the Fischer projection. Place the NH₂ group and the phenyl group on the horizontal lines (coming out of the plane), and the methyl group and hydrogen on the vertical lines (going into the plane). Ensure the stereochemistry matches the original molecule.

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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 diagrams, vertical lines represent bonds that project behind the plane of the page, while horizontal lines represent bonds that project out towards the viewer. This format is especially common for carbohydrates and amino acids, allowing for easy visualization of chiral centers and their configurations.

Chirality and Stereocenters

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of one or more stereocenters. A stereocenter is typically a carbon atom bonded to four different substituents, leading to two possible configurations (R and S). Understanding chirality is crucial for accurately drawing Fischer projections, as it determines the spatial arrangement of the substituents around the stereocenter.

Configuration Notation (R/S)

The R/S notation is a system used to specify the absolute configuration of chiral centers in molecules. To assign R (rectus) or S (sinister) configuration, one must prioritize the substituents attached to the stereocenter based on atomic number, with higher atomic numbers receiving higher priority. This systematic approach is essential for accurately representing the stereochemistry in Fischer projections and understanding the molecule's reactivity and interactions.

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Related Practice

Textbook Question

Convert the line-angle drawings into Fischer projections.

(a)

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

Convert the following perspective formulas to Fischer projections.

(c)

(d)

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)

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Draw Fischer projections of the following molecules.(c)

Key Concepts

Fischer Projections

Chirality and Stereocenters

Configuration Notation (R/S)

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Draw Fischer projections of the following molecules.
(c)