Which of the following is least reactive in a nucleophilic substitution reaction?

Question

Which of the following is least reactive in a nucleophilic substitution reaction? (A)  (CH3)3C-Cl  (B)  CH2=CHCl  (C)  CH3CH2Cl  (D)  CH2=CHCH2Cl

Tardigrade Admin · Accepted Answer

Chlorine of vinyl chloride (CH2=CHCl) is non-reactive (less reactive) towards nucleophile in nucleophilic substitution reaction because it shows the following resonating structure due to +M effect of ?Cl atom. In structure II, Cl-atom have positive charge and partial double bond character with C of vinyl group, so it is more tightly attracted towards the nucleus and it does not get replaced by nucleophile in SN reaction.

Q. Which of the following is least reactive in a nucleophilic substitution reaction?

$(C H_{3})_{3} C - Cl$

$C H_{2} = C H Cl$

$C H_{3} C H_{2} Cl$

$C H_{2} = C H C H_{2} Cl$

Q. Which of the following is least reactive in a nucleophilic substitution reaction?

(CH3​)3​C−Cl

CH2​=CHCl

CH3​CH2​Cl

CH2​=CHCH2​Cl

$(C H_{3})_{3} C - Cl$

$C H_{2} = C H Cl$

$C H_{3} C H_{2} Cl$

$C H_{2} = C H C H_{2} Cl$