Chapter 12, Problem 12.33P

Interpretation Introduction

Interpretation:

All stereoisomers that can be produced in the given reaction are to be drawn.

Concept introduction:

Heat or light causes the weak ${\text{C-N}}_{\text{2}}$ bond to break. In Step 1, the ${\text{C-N}}_{\text{2}}$ bond breaks when energy is absorbed from light and carbene is produced. Carbenes are typically highly electrophilic due to the lack of an octet. Carbene reacts with the alkene to generate the three-membered ring. The reaction produces a mixture of stereoisomers as alkene is planar, and the electrophile can be added to either face of the alkene. One stereoisomer is produced by the addition of the carbene to one face, and the second is produced by addition to the other face.