First slide

Alkenes

Question

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

Moderate

A

${Cl}_{3}^{} {CCH}_{2}^{} {CH}_{2}^{} Cl$
B

${Cl}_{3}^{} CCH (Cl) {CH}_{3}^{}$
C

${Cl}_{2}^{} CHCH (Cl) {CH}_{2}^{} Cl$
D

${Cl}_{2}^{} {CHCH}_{2}^{} {CHCl}_{2}^{}$

Solution

(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
${CCl}_{3}^{} - CH = C H_{2}^{} \overset{H^{+}}{\to} {CCl}_{3}^{} - \overset{+}{C} H - {CH}_{3}^{}$
Less stable
Instead the addition follows anti-Markovnikoff’s rule because primary carbonium ion becomes relatively more stable.

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