The addition of HCl to 3,3,3-trichloropropene gives:

(1) CCl3 is a strongly electron – withdrawing group. The addition of HCl to double bond of 3,3,3-trichloropropene does not follow the Markovnikoff’s rule because intermediate secondary carbonium ion is destabilized by the – I effect if CCl3 groupCCl3 −CH=CH2 →H+CCl3 −C+H−CH3 Less stableInstead the addition follows anti-Markovnikoff’s rule because primary carbonium ion becomes relatively more stable.