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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7:09 minutes

Problem 35a

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)

Verified step by step guidance

Step 1: Analyze the given structure. The molecule is a Fischer projection with an aldehyde group (CHO) at the top, two hydroxyl groups (OH) on the horizontal bonds, and a primary alcohol group (CH2OH) at the bottom. The central carbons are stereocenters.

Step 2: Determine the stereoisomers. Each stereocenter can have two configurations (R or S). For two stereocenters, the total number of stereoisomers is 2^n, where n is the number of stereocenters. Here, n = 2, so there are 4 stereoisomers.

Step 3: Draw all stereoisomers. To do this, assign different combinations of R and S configurations to the two stereocenters. For example, (R,R), (R,S), (S,R), and (S,S). Represent each configuration using Fischer projections.

Step 4: Label each structure as chiral or achiral. A molecule is chiral if it has a non-superimposable mirror image. Check for symmetry in each stereoisomer to determine chirality.

Step 5: Determine the relationships between the stereoisomers. Compare each pair of stereoisomers. If they are non-superimposable mirror images, they are enantiomers. If they are not mirror images but differ in configuration, they are diastereomers.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This can lead to different physical and chemical properties. The two main types of stereoisomers are enantiomers, which are non-superimposable mirror images, and diastereomers, which are not mirror images of each other.

Chirality

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral molecule typically has at least one carbon atom bonded to four different substituents, creating two distinct forms (enantiomers). In contrast, achiral molecules can be superimposed on their mirror images and do not exhibit this property.

Relationship between Stereoisomers

The relationship between stereoisomers is crucial for understanding their interactions and properties. Enantiomers have identical physical properties except for their interaction with polarized light and reactions in chiral environments. Diastereomers, on the other hand, differ in physical properties and reactivity, making their relationships more complex. Identifying these relationships helps in predicting the behavior of compounds in various chemical contexts.

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Related Practice

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

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)

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

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.

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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)

Key Concepts

Stereoisomerism

Chirality

Relationship between Stereoisomers

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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)