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 group

${\mathrm{CCl}}_3^{ }-\mathrm{CH}=\mathrm{C}{\mathrm{H}}_2^{ }\stackrel{{\mathrm{H}}^{+}}{\to }{\mathrm{CCl}}_3^{ }-\stackrel{+}{\mathrm{C}}\mathrm{H}-{\mathrm{CH}}_3^{ }$

Less stable

Instead the addition follows anti-Markovnikoff’s rule because primary carbonium ion becomes relatively more stable.