a) i) Write the equations for the steps in $S_{N} 1$ mechanism of the conversion of tert.butyl bromide into tert.butyl alcohol.
ii) Haloarences are less reactive towards nucleophilic substitution reactions than Haloalkanes. Give a reason.
b) Complete the following equations :
i) $C_{2} H_{5} O H + S O C l_{2} \to . . . . . . . . . . . . . . . . . . . . . . . . . . .$
ii) Please find above image.

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Solution

a) i) The equations for the steps in $S_{N}^{1}$ mechanism of the conversion of $t e r t . b u t y l b r o m i d e$ into $t e r t b u t y l a l c o h o l$ are given below.
$(C H_{3})_{3} C - B r \to (C H_{3})_{3} C^{+} + B r^{-}$
$(C H_{3})_{3} C^{+} + O H^{-} \to (C H_{3})_{3} C B r$
ii) Haloarenes are less reactive towards nucleophilic substitution reactions than Haloalkanes. Give a reason. In haloarenes, the $C - X$ bond has partial double bond character as the lone pair of electrons on halogen is in resonance with benzene ring. Hence, $C - X$ bond is difficult to break in haloarenes. In haloalkanes, $C - X$ bond is single bond and is easy to break.
b) The completed equations equations are given below.
i) $C_{2} H_{5} O H + S O C l_{2} \to C_{2} H_{5} - C l + S O_{2} ↓ + H C l ↓$
ii) $2 C_{6} H_{5} - C l + 2 N a e t h e r - -- \to C_{6} H_{5} - C_{6} H_{5} + 2 N a C l$

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