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

6. Thermodynamics and Kinetics

Carbocation Stability

Organic Chemistry

6. Thermodynamics and Kinetics

Carbocation Stability

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2:53 minutes

Problem 6c

Textbook Question

Identify the more stable carbocation in each pair.
(c)

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Analyze the structure of each carbocation in the pair. Carbocation stability is influenced by factors such as the number of alkyl groups attached to the positively charged carbon (hyperconjugation), resonance stabilization, and inductive effects.

Determine the degree of substitution for each carbocation. A tertiary carbocation (positively charged carbon attached to three alkyl groups) is more stable than a secondary carbocation, which is more stable than a primary carbocation, due to hyperconjugation and inductive effects.

Check for resonance stabilization. If one of the carbocations has a positive charge that can be delocalized through resonance (e.g., adjacent to a double bond or aromatic ring), it will be more stable than a carbocation without resonance stabilization.

Evaluate any inductive effects. Electron-donating groups near the carbocation can stabilize the positive charge, while electron-withdrawing groups can destabilize it. Compare the groups attached to the carbocation in each pair.

Combine all the factors (degree of substitution, resonance, and inductive effects) to identify which carbocation in the pair is more stable. The carbocation with the greatest stabilization from these factors will be the more stable one.

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Key Concepts

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

Carbocation Stability

Carbocations are positively charged carbon species that are classified based on their degree of substitution: primary, secondary, and tertiary. Tertiary carbocations are the most stable due to hyperconjugation and the inductive effect from surrounding alkyl groups, which help to disperse the positive charge. Understanding this stability hierarchy is crucial for predicting the reactivity and formation of carbocations in organic reactions.

Hyperconjugation

Hyperconjugation is a stabilizing interaction that occurs when the electrons in a sigma bond (usually C-H or C-C) interact with an adjacent empty p-orbital or a positively charged carbon. This interaction allows for the delocalization of charge, which stabilizes the carbocation. The more alkyl groups attached to the carbocation, the greater the hyperconjugation effect, leading to increased stability.

Inductive Effect

The inductive effect refers to the electron-donating or withdrawing effects of substituents through sigma bonds. Alkyl groups are electron-donating and can stabilize a carbocation by pushing electron density towards the positively charged carbon. This effect is particularly significant in determining the stability of carbocations, as more electron-donating groups lead to greater stabilization of the positive charge.

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Identify the more stable carbocation in each pair.(c)

Key Concepts

Carbocation Stability

Hyperconjugation

Inductive Effect

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Identify the more stable carbocation in each pair.
(c)