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

16. Conjugated Systems

Stability of Conjugated Intermediates

Organic Chemistry

16. Conjugated Systems

Stability of Conjugated Intermediates

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4:18 minutes

Problem 12

Textbook Question

Name the following dienes and rank them from most stable to least stable.

Verified step by step guidance

Identify the structure of each diene in the image. Look for the presence of conjugated double bonds, isolated double bonds, or cumulated double bonds.

Apply the IUPAC naming rules to each diene. Start by identifying the longest carbon chain that includes both double bonds, and number the chain starting from the end closest to the first double bond.

Determine the position of each double bond in the chain and use the appropriate locants in the name. Remember to use the suffix '-diene' to indicate the presence of two double bonds.

Evaluate the stability of each diene. Conjugated dienes (where double bonds are separated by a single bond) are generally more stable than isolated dienes (where double bonds are separated by more than one single bond) and cumulated dienes (where double bonds are adjacent).

Rank the dienes from most stable to least stable based on their structure. Conjugated dienes are typically the most stable due to resonance stabilization, followed by isolated dienes, and cumulated dienes are usually the least stable.

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Key Concepts

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

Diene Stability

Diene stability refers to the relative stability of compounds containing two double bonds. Factors influencing this stability include the degree of substitution on the double bonds, with more substituted dienes generally being more stable due to hyperconjugation and the inductive effect. Additionally, the presence of conjugation, where double bonds are separated by a single bond, can enhance stability through resonance.

Conjugation

Conjugation occurs when alternating single and double bonds allow for the delocalization of π electrons across the molecule. This delocalization stabilizes the molecule, making conjugated dienes more stable than isolated double bonds. The stability from conjugation is a key factor when ranking the stability of different diene structures.

Substitution Patterns

The substitution pattern of a diene significantly affects its stability. Dienes can be classified as 1,2-disubstituted, 1,3-disubstituted, or unsubstituted, with 1,3-disubstituted dienes typically being the most stable due to increased hyperconjugation and steric effects. Understanding these patterns is essential for accurately ranking the stability of the given dienes.

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