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

Previous problemNext problem

3:59 minutes

Problem 17e

Textbook Question

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
(e)

Verified step by step guidance

Step 1: Understand the Fischer projection. A Fischer projection is a two-dimensional representation of a molecule where the vertical line represents the carbon chain, and the horizontal lines represent substituents coming out of the plane of the paper. The cross represents an asymmetric carbon atom.

Step 2: Identify the asymmetric carbon atom in (R)-glyceraldehyde. In the provided structure, the second carbon (C2) is the asymmetric carbon because it is bonded to four different groups: a hydroxyl group (-OH), a hydrogen atom (-H), a methyl group (-CH2OH), and an aldehyde group (-CHO).

Step 3: Arrange the carbon chain vertically. In the Fischer projection, the aldehyde group (-CHO) is placed at the top (C1), the hydroxymethyl group (-CH2OH) is placed at the bottom (C3), and the asymmetric carbon (C2) is in the middle.

Step 4: Assign the substituents on the asymmetric carbon (C2). For (R)-glyceraldehyde, the hydroxyl group (-OH) is placed on the right side, and the hydrogen atom (-H) is placed on the left side in the Fischer projection. This arrangement corresponds to the (R)-configuration.

Step 5: Draw the Fischer projection. The vertical line represents the carbon chain with C1 at the top and C3 at the bottom. The horizontal line at C2 shows the substituents: -OH on the right and -H on the left. Ensure the numbering follows the IUPAC convention from top to bottom.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 important for visualizing the configuration of chiral centers in carbohydrates and amino acids.

Chirality and Asymmetric Carbon

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 asymmetric carbon atoms. An asymmetric carbon, or chiral center, is a carbon atom bonded to four different groups, leading to two possible configurations (R or S). Understanding chirality is crucial for determining the optical activity and biological function of organic compounds.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds, ensuring that each compound has a unique and descriptive name. The rules dictate how to identify the longest carbon chain, number the carbon atoms, and name substituents. In the context of Fischer projections, proper IUPAC naming helps in accurately representing the structure and configuration of the molecule, such as (R)-glyceraldehyde.

Watch next

Master Introduction to different projections. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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)

Textbook Question

a. Are d-erythrose and l-erythrose enantiomers or diastereomers?

b. Are l-erythrose and l-threose enantiomers or diastereomers?

Textbook Question

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

(e)

(f)

Textbook Question

For each structure,

1. draw all the stereoisomers.

2. label each structure as chiral or achiral.

3. give the relationships between the stereoisomers (enantiomers, diastereomers).

(a)

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)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.(e)

Key Concepts

Fischer Projections

Chirality and Asymmetric Carbon

IUPAC Nomenclature

Watch next

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
(e)