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

19. Reactions of Aromatics: EAS and Beyond

Side-Chain Halogenation

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Side-Chain Halogenation

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Multiple Choice

Which of the following does NOT explain why reactive intermediates at the benzylic position are relatively stable?

A benzylic C–X bond will break faster to form a carbocation.

The benzylic C–H bond has a lower BDE.

The benzylic C–H bond has a lower pK_a value.

The original benzylic C–H bond has a shorter bond length.

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Verified step by step guidance

Understand the concept of benzylic position: The benzylic position refers to the carbon atom directly attached to a benzene ring. Reactive intermediates at this position, such as carbocations, radicals, or carbanions, are often more stable due to resonance stabilization with the aromatic ring.

Examine the first option: A benzylic C–X bond will break faster to form a carbocation. This is true because the resulting carbocation can be stabilized by resonance with the benzene ring, making the bond easier to break.

Consider the second option: The benzylic C–H bond has a lower bond dissociation energy (BDE). A lower BDE indicates that the bond is weaker and easier to break, which can facilitate the formation of reactive intermediates.

Evaluate the third option: The benzylic C–H bond has a lower pKa value. A lower pKa value suggests that the hydrogen is more acidic, meaning it can be removed more easily to form a carbanion, which can also be resonance-stabilized.

Analyze the fourth option: The original benzylic C–H bond has a shorter bond length. Bond length is not directly related to the stability of reactive intermediates. Therefore, this option does not explain the stability of reactive intermediates at the benzylic position.