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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3:07 minutes

Problem 20e,f

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the pair of compounds in part (e). Both compounds are bicyclic structures with a chlorine atom attached. Observe the orientation of the chlorine atom relative to the plane of the molecule. One compound has the chlorine atom in an axial position, while the other has it in an equatorial position. This indicates that the two compounds are stereoisomers, specifically conformational isomers.

Step 2: For part (e), confirm whether the compounds are enantiomers or diastereomers. Since the compounds differ in the spatial arrangement of the chlorine atom but are not mirror images, they are diastereomers.

Step 3: Analyze the pair of compounds in part (f). Both compounds are Fischer projections of sugar molecules. Observe the orientation of the hydroxyl (-OH) groups and hydrogen atoms on the chiral centers. In the first compound, the hydroxyl groups are on the right side, while in the second compound, the hydroxyl groups are on the left side.

Step 4: For part (f), determine the relationship between the two compounds. Since the compounds are mirror images of each other, they are enantiomers. Enantiomers are non-superimposable mirror images and have opposite configurations at all chiral centers.

Step 5: Summarize the relationships: In part (e), the compounds are diastereomers due to different spatial arrangements of the chlorine atom. In part (f), the compounds are enantiomers because they are mirror images of each other.

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Key Concepts

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

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In organic chemistry, stereoisomers are compounds that have the same molecular formula and connectivity but differ in the orientation of their atoms in space. Understanding stereochemistry is crucial for analyzing the relationship between the two compounds shown, as their three-dimensional shapes can influence their reactivity and properties.

Conformational Analysis

Conformational analysis involves studying the different spatial arrangements (conformations) of a molecule that can be achieved by rotation around single bonds. The two compounds in the question likely represent different conformers of the same molecule, which can have distinct energy levels and stability. Recognizing these conformations helps in understanding the relationship between the compounds and predicting their behavior in chemical reactions.

Substituent Effects

Substituent effects refer to how different groups attached to a carbon skeleton influence the properties and reactivity of a molecule. In the context of the compounds shown, the position of the chlorine atom (Cl) can significantly affect the molecule's stability and reactivity. Analyzing how the substituent's position alters the overall structure is essential for determining the relationship between the two compounds.

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Related Practice

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

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 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)

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)

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

Key Concepts

Stereochemistry

Conformational Analysis

Substituent Effects

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