Free-Radical mechanism Initiation: RO-OR 2 RO' RO+HBr Br+ROH Propagation:i) +Br' H-Br Br
Free-Radical Mechanism Initiation: Propagation: i) ii) RO-OR 2 RO RO + HBr Br + ROH + Br Br Br + H-Br H Br + Br . . . . . .
Addition of Br2 Br2 Br Br
Addition of Br2 Br Br Br2
A Similar Mechanism to the Addition of HBr? H :Br: Br Possible Br mechanism? H H C2004 Thomson-Brooks/Cole
A Similar Mechanism to the Addition of HBr?
Trans is formed exclusively (No cis is formed) H Br H H Br-Br Br H Br Br Cyclopentene trans-1,2-Dibromo- cis-1,2-Dibromo- cyclopentane cyclopentane (Sole product) (Not formed) C2004 Thomson-Brooks/Cole
Trans is formed exclusively (No cis is formed)
Carbocation can be Stabilized by Neighboring Br :Br: :Br: :Br-Br: C=C An alkene A bromonium ion :Br: 2004 Thomson/Brooks Cole
Carbocation can be Stabilized by Neighboring Br