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Radical HBr addition (alkenes & alkynes) Reagents:
HBr+ ROOR, hv (light), or heat (anti-markonikov)

Carbene addition to alkenes Reagents
CHCl3 or CHBr3 + strong base ( KOTBU, NaOH) (cyclopentane formation)

Simmons - Smith Reagents:
CH2I2 + (Zn(Cu)) + ether solvent

Polymerization of alkenes Reagents:
heat + peroxide (free- rad) or H2SO4 OR HF + BF3, H2O (cationic)