Question

Which alkyl halide is preferentially hydrolysed by $S_{N}1$mechanism

• A. $(CH_{3})_{3}CCl$
• B. $CH_{3}CH_{2}CH_{2}Cl$
• C. $CH_{3}CH_{2}Cl$
• D. $CH_{3}Cl$

Answer 1

Answer: (A)

$(CH_{3})_{3}CCl$

Answer 2

$S_{N}1$mechanism

(i) $(CH_{3})_{3}C - Cl\overset{\quad\quad}{\rightarrow}(CH_{3})_{3}C^{+} + Cl^{-}$ $$3{^\circ}carbocation$$

(ii) $(CH_{3})_{3}C^{+}\overset{\rightarrow}{\quad - OH\quad}(CH_{3})_{3}C - OH$

For $S_{N}1$mechanism the reactivity of carbocaiton are 3° > 2° > 1°