A student reacted NBS with 1-methylcyclopent-1-ene under a sunlamp.


(i) Draw all resonance forms of the three possible allylic free radical intermediates of the reaction
(ii) Label the three intermediates 1 through 3 (1 is the most stable; 3 is the least stable)
(iii) Draw the products that could be obtained from the reaction

• A. (i)-(iii)
• B. (i)-(iii)
• C. (i)-(iii)
• D. (i)-(iii)

Answer: (A)