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

Constitutional Isomers vs. Stereoisomers

Organic Chemistry

5. Chirality

Constitutional Isomers vs. Stereoisomers

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1:27 minutes

Problem 10a

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).
(a)

Verified step by step guidance

Identify the chiral centers in the molecule. A chiral center is a carbon atom that is attached to four different atoms or groups. Look for tetrahedral carbons with four distinct substituents.

Once the chiral centers are identified, assign priorities to the four groups attached to each chiral center based on the Cahn-Ingold-Prelog (CIP) priority rules. These rules prioritize groups based on atomic number, with higher atomic numbers receiving higher priority.

Orient the molecule so that the group with the lowest priority (priority 4) is pointing away from you (into the plane of the paper or screen). This is typically represented with a dashed wedge.

Determine the configuration of the chiral center by tracing a path from priority 1 to priority 2 to priority 3. If the path is clockwise, the configuration is R (rectus). If the path is counterclockwise, the configuration is S (sinister).

Draw the 3-D representation of the molecule, using solid wedges to represent bonds coming out of the plane (toward the viewer) and dashed wedges for bonds going into the plane (away from the viewer). Ensure that the stereochemistry (R or S) is correctly represented for each chiral center.

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Key Concepts

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

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral center, typically a carbon atom, is bonded to four different substituents, leading to two distinct enantiomers. Understanding chirality is crucial for predicting the behavior of molecules in biological systems, as enantiomers can have different effects.

3-D Molecular Representation

3-D molecular representation involves depicting the spatial arrangement of atoms within a molecule, which is essential for understanding its reactivity and interactions. Techniques such as ball-and-stick models or wedge-dash notation are used to illustrate the three-dimensional structure, highlighting bond angles and the orientation of substituents around chiral centers.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this arrangement affects their chemical properties and reactions. It encompasses concepts like chirality, geometric isomerism, and conformational isomerism. A solid grasp of stereochemistry is vital for accurately drawing and interpreting 3-D representations of molecules, especially those with chiral centers.

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Related Practice

Textbook Question

Draw all the stereoisomers for each of the following:

g. 1,3-dichlorocyclohexane

h. 1,4-dichlorocyclohexane

Textbook Question

Draw all possible stereoisomers for each of the following. Indicate those compounds for which no stereoisomers are possible.

e. 1-bromo-4-chlorocyclohexane

f. 1,2-dimethylcyclopropane

Textbook Question

In contrast to Assessment 6.63, the following compounds should be easily separable using standard methods. Why?

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(b)

Multiple Choice

Which of the following describes stereoisomers?

Textbook Question

Give the relationships between the following pairs of structures. The possible relationships are as follows: same compound, cis-trans isomers, constitutional (structural) isomers, and not isomers (different molecular formula).

(a) CH₃CH₂CH₂CH₃ and (CH₃)₃CH

(b) CH₂=CH–CH₂Cl and CHCl=CH–CH₃

Textbook Question

For each pair of structures, determine whether they represent different compounds or a single compound.

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