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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1:58 minutes

Problem 25a,b,c

Textbook Question

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

(a)
(b)
(c)

Verified step by step guidance

Examine the connectivity of atoms in both structures. Check if the atoms are connected in the same sequence or if there are differences in the bonding pattern.

Compare the spatial arrangement of atoms in the structures. Determine if they are mirror images of each other (enantiomers) or if they differ in configuration at one or more stereocenters (diastereomers).

Check for any differences in functional groups or substituents. If the structures differ only in the position of a substituent or functional group, they may be positional isomers.

Determine if the structures are identical by superimposing them. If they are identical in both connectivity and spatial arrangement, they are the same compound.

If none of the above relationships apply, consider whether the structures are constitutional isomers (same molecular formula but different connectivity) or unrelated compounds.

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Key Concepts

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

Structural Isomerism

Structural isomerism refers to compounds that have the same molecular formula but differ in the connectivity of their atoms. This can lead to different physical and chemical properties. Understanding structural isomers is crucial for analyzing relationships between different chemical structures, as it helps identify how variations in connectivity can affect reactivity and stability.

Stereoisomerism

Stereoisomerism occurs when compounds have the same molecular formula and connectivity but differ in the spatial arrangement of atoms. This includes geometric isomers (cis/trans) and optical isomers (enantiomers). Recognizing stereoisomers is essential for understanding how the three-dimensional arrangement of atoms influences the behavior of molecules in biological systems and chemical reactions.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying functional groups is vital for determining the reactivity and properties of organic compounds. The relationship between structures often hinges on the presence and type of functional groups, which dictate how molecules interact with each other.

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Related Practice

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.

Textbook Question

Give the relationship between the following pairs of structures. The possible relationships are:

same compound

constitutional isomers (structural isomers)

cis-trans isomers

not isomers (different molecular formula)

(j)

(k)

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).

(c)

(d)

Textbook Question

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(a)

Textbook Question

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(e)

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Give the relationship between the following pairs of structures. The possible relationships are:same compoundconstitutional isomers (structural isomers)cis-trans isomersnot isomers (different molecular formula)(a) (b) (c)

Key Concepts

Structural Isomerism

Stereoisomerism

Functional Groups

Watch next

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

(a)
(b)
(c)