Reactions at the benzylic position typically occur faster than than the same reactions at other carbons, and this allows us to do special selective reactions .

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The question discusses benzylic reactions and asks us to select the appropriate phrases to complete the statement.
Option 1: “faster than” — This is correct in general terms. Reactions at the benzylic position often proceed more rapidly than analogous reactions at non-benzylic (alkyl) positions because the benzylic intermediates (carbenium/benzyl cations, radicals, or transition states) are resonance-stabilized by the adjacent aromatic ring. This stabilization lowers activation barriers and speeds up reaction rates compared to non-benzylic carbons.
Option 2: “special selective reactions” — This is also reasonable. Because benzylic positions are activated and there is resonance stabilization, chemists can exploit this to achieve selective transformations that favor benzylic substitution, oxidation, or functionalization over other positions. The chemistry often allows for regioselective or chemoselective outcomes (e.g., benzylic bromination, oxidation to benzaldehydes/benzoic acids, or selective C–H activation at the benzylic site) due to the relatively lower C–H bond dissociation energy and stabilized intermediates.
However, to ensure clarity, it’s worth noting that while benzylic sites are typically more reactive and enable selective transformations, the exact rates and selectivity depend on the specific reaction type, substituents on the ring, and the reagents used. In some circumstances, other factors (steric hindrance, directing effects, or competing pathways) can influence both speed and selectivity.
Overall, both phrases—“faster than” and “special selective reactions”—accurately capture the common themes of benzylic reactivity: accelerated rates due to stabilization, and the ability to achieve selective transformations at the benzylic position.

CHE 008B A01 SS1 2025 Lecture 5 - Benzylic Reactivity

Reactions at the benzylic position typically occur faster than than the same reactions at other carbons, and this allows us to do special selective reactions .

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