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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1:45 minutes

Problem 59c,d

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)

Verified step by step guidance

Step 1: Begin by analyzing the molecular formulas of the two structures in each pair. Determine if the molecular formulas are identical or different. If they are different, the structures are not isomers.

Step 2: If the molecular formulas are identical, examine the connectivity of atoms in each structure. If the connectivity differs, the structures are constitutional (structural) isomers.

Step 3: If the connectivity is the same, check for stereoisomerism. Look for differences in spatial arrangement, such as cis-trans isomerism around double bonds or rings.

Step 4: If the spatial arrangement and connectivity are identical, the structures represent the same compound.

Step 5: Summarize the relationship for each pair based on the analysis above, ensuring clarity in distinguishing between the possible relationships: same compound, cis-trans isomers, constitutional isomers, or not isomers.

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Key Concepts

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

Isomerism

Isomerism refers to the phenomenon where two or more compounds have the same molecular formula but differ in the arrangement of atoms. This can lead to different physical and chemical properties. The main types of isomers include structural isomers, which differ in the connectivity of atoms, and stereoisomers, which have the same connectivity but differ in spatial arrangement.

Cis-Trans Isomerism

Cis-trans isomerism is a specific type of stereoisomerism that occurs in compounds with restricted rotation around a double bond or a ring structure. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. This geometric distinction can significantly affect the physical properties of the compounds.

Constitutional Isomers

Constitutional isomers, also known as structural isomers, are compounds that have the same molecular formula but differ in the connectivity of their atoms. This means that the atoms are bonded together in different ways, leading to distinct compounds with unique properties. Understanding constitutional isomers is crucial for analyzing relationships between different chemical structures.

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Related Practice

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)

(a)

(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)

(j)

(k)

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)

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

(f)

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

(h)

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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)

Key Concepts

Isomerism

Cis-Trans Isomerism

Constitutional Isomers

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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)