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

11. Radical Reactions

Radical Selectivity

Organic Chemistry

11. Radical Reactions

Radical Selectivity

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7:29 minutes

Problem 18a

Textbook Question

Using the bond-dissociation energies in Table 5.6,
(a) predict whether or not a fluorine radical would be selective for forming a single radical from propane.

Verified step by step guidance

Understand the concept of bond-dissociation energy: Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. It is a measure of the bond strength.

Identify the relevant bond-dissociation energies: Look up the bond-dissociation energies for the C-H bonds in propane and the C-H bonds in the potential radical products. This will help determine which bond is most likely to be broken by the fluorine radical.

Consider the reactivity of fluorine radicals: Fluorine radicals are highly reactive due to their high electronegativity and small size. They tend to react quickly and may not be very selective in their reactions.

Compare the bond-dissociation energies: Analyze the bond-dissociation energies of the primary and secondary C-H bonds in propane. Typically, secondary C-H bonds have lower bond-dissociation energies compared to primary C-H bonds, making them more likely to be broken.

Predict the selectivity: Based on the bond-dissociation energies and the reactivity of fluorine radicals, predict whether the fluorine radical will preferentially form a single radical from propane or if it will react non-selectively with multiple C-H bonds.

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Key Concepts

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

Bond-Dissociation Energy

Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. It is a measure of bond strength and varies depending on the atoms involved and the molecular environment. Understanding these energies helps predict the stability of radicals formed during chemical reactions.

Radical Selectivity

Radical selectivity refers to the preference of a radical to react with certain types of bonds over others. This selectivity is influenced by factors such as bond-dissociation energies and steric effects. In the context of fluorine radicals, their high reactivity can lead to less selectivity, making it crucial to analyze bond energies to predict reaction outcomes.

Propane Structure

Propane is a three-carbon alkane with the molecular formula C3H8. It consists of primary and secondary hydrogen atoms, which differ in their bond-dissociation energies. Understanding the structure of propane is essential for predicting which hydrogen atoms are more likely to be abstracted by a radical, influencing the formation of specific radicals.

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Using the bond-dissociation energies in Table 5.6, (a) predict whether or not a fluorine radical would be selective for forming a single radical from propane.

Key Concepts

Bond-Dissociation Energy

Radical Selectivity

Propane Structure

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Using the bond-dissociation energies in Table 5.6,
(a) predict whether or not a fluorine radical would be selective for forming a single radical from propane.