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. <img class="img-fluid question-image" alt="image" src="https://cdn.tardigrade.in/img/question/chemistry/173f44e861c48aaeac0fce9c56ac3138-.png" /> 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

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

$C H_{2} = C H Cl$

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

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