[amcavoy]

Can someone explain why the addition of NBS and light to cyclopentene yields two enantiomers?  It was my understanding that the bromine atom would be added in the allylic position to the left and to the right of the double bond, which form the same molecules.

[sondakem]

Even though we draw molecules as flat entities, they exist as three dimensional objects.  Try drawing a projection model or make an actual 3D model.

[AWK]

Can someone explain why the addition of NBS and light to cyclopentene yields two enantiomers?  It was my understanding that the bromine atom would be added in the allylic position to the left and to the right of the double bond, which form the same molecules.

Seldom radical mechanism is stereospecific