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The addition of HCl to 3,3,3-trichloropropene gives:
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a
Cl3 CCH2 CH2 Cl
b
Cl3 CCH(Cl)CH3
c
Cl2 CHCH(Cl)CH2 Cl
d
Cl2 CHCH2 CHCl2
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Correct option is A
(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.Talk to our academic expert!
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