a) Write equations for the steps in $S_{N} 1$ mechanism of the conversion of tert. butyl bromide into tert. butyl alcohol.
b) Identify the products $A, B$ and $C$ in the following equation

$C H_{3} O H R e d P - -- \to C l_{2} A N a I - ----- \to d r y a c e t o n e B C_{6} H_{5} I - -------- \to N a a n d d r y e t h e r C$ .

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Solution

a) Write equations for the steps in $S_{N} 1$ mechanism of the conversion of tert. butyl bromide into tert. butyl alcohol.
$(C H_{3})_{3} C - B r s l o w s t e p - ---- \to (C H_{3})_{3} C^{+} + B r^{-}$
$(C H_{3})_{3} C^{+} + O H^{-} \to (C H_{3})_{3} C - O H$
b)
$C H_{3} O H R e d P - -- \to C l_{2} C H_{3} - C l A N a I - ------ \to d r y a c e t o n e C H_{3} - I B C_{6} H_{5} I - --------- \to N a a n d d r y e t h e r C H_{3} - C_{6} H_{5} C$
Methanol reacts with red $P / C l_{2}$ to form methyl chloride. $C l$ is then replaced with $I$ by reaction with $N a I / d r y a c e t o n e$ In the final step, $C H_{3} - I$ is coupled with $C_{6} H_{5} - I$ to form $C_{6} H_{5} - C H_{3}$ . The reaction is called the Wurtz–Fittig reaction.

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