Question

Arrange the following compounds in order of their reactivity towards $S_{N}2$reaction.

(i) $CH_{3}(CH_{2})_{3}CH_{2}Br$

(ii) $(CH_{3})_{2}CHCH_{2}CH_{2}Br$

(iii) $CH_{3}CH_{2} - \overset{\overset{CH_{3}}{|}}{C}H - CH_{2}Br$

(iv) $CH_{3} - \overset{\overset{CH_{3}}{|}}{\underset{\underset{CH_{3}}{|}}{C}} - CH_{2}Br$

• A. (i) > (ii) > (iii) > (iv)
• B. (ii) > (iii) > (iv) > (i)
• C. (iii) > (i) > (ii) > (iv)
• D. (iv) > (ii) > (i) > (iii)

Answer 1

Answer: (D)

(iv) > (ii) > (i) > (iii)

Answer 2

$CH_{3}CH_{2}CH = CH_{2} + HBr\overset{\quad peroxide\quad}{\rightarrow}CH_{3}CH_{2}CH_{2}CH_{2}Br$