Solution (source code)

= Solution

\b[Styrene, benzoyl peroxide and TEMPO] provide the required radical addition–trapping sequence. Heating the peroxide breaks its O–O bond into benzoyloxy radicals. Before decarboxylation, $\mathrm{PhCO_2^{\bullet}}$ can add to styrene's terminal carbon, generating the resonance-stabilized radical $\mathrm{PhCO_2CH_2\dot CHPh}$. Coupling with the oxygen-centred TEMPO radical then gives $\mathrm{PhCO_2CH_2CH(Ph)-O-TEMPO}$, the benzoate-protected alkoxyamine A.

The connectivity distinguishes this route from initiators that leave a carbon-based radical fragment at the chain end. Competition with benzoyloxy-radical decarboxylation affects yield, so this is a plausible preparation rather than a claim of exclusive product formation. Subsequent benzoate cleavage reveals B's hydroxyl group without requiring rupture of its alkoxyamine linkage.