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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2:00 minutes

Problem 4d

Textbook Question

Which species in each pair is more stable?
d.

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Identify the two species in the pair and determine their structures. Look for any differences in functional groups, hybridization, or resonance structures.

Examine the electronic effects such as inductive effects, resonance, and hyperconjugation that might stabilize or destabilize each species.

Consider the steric factors that might affect stability. Check if there are any steric hindrances or strain in the molecular structure.

Evaluate the hybridization of the atoms involved. Generally, more s-character in hybrid orbitals (e.g., sp vs. sp3) can lead to greater stability due to lower energy.

Analyze the overall molecular stability by considering all the factors together, including electronic effects, steric factors, and hybridization, to determine which species is more stable.

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Key Concepts

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

Stability of Chemical Species

The stability of chemical species refers to their tendency to maintain their structure and resist change. Factors influencing stability include the energy of the species, resonance stabilization, and steric hindrance. More stable species typically have lower energy and are less reactive, making them less likely to undergo chemical transformations.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. A molecule with multiple resonance structures can distribute its electron density more evenly, leading to increased stability. The actual structure of the molecule is a hybrid of these resonance forms, which helps in predicting reactivity and stability.

Steric Hindrance

Steric hindrance refers to the repulsion between bulky groups within a molecule that can affect its stability and reactivity. When atoms or groups are too close together, they can create strain, making the molecule less stable. Understanding steric effects is crucial for predicting the behavior of different species in chemical reactions.

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Related Practice

Textbook Question

The benzene ring alters the reactivity of a neighboring group in the benzylic position much as a double bond alters the reactivity of groups in the allylic position.

Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates.

c. Which of the following reactions will have the faster rate and give the better yield? Use a drawing of the transition state to explain your answer.