: Because the resulting radical is so stable, the benzylic C–HC–H bond is unusually weak (approx. ) compared to standard primary ( ) or even tertiary ( C–HC–H
: In organic synthesis, the stability of the benzyl radical is leveraged for site-specific functionalization, such as installing leaving groups or enabling complex cyclization cascades in natural product synthesis. Comparative Stability benzyl radical
: Due to the low bond dissociation energy, benzylic positions are highly reactive toward free-radical substitutions, such as bromination using N-bromosuccinimide (NBS) . : Because the resulting radical is so stable,