The following are possible syntheses of pheny | vedclass

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(A) The synthesis of ethers via the Williamson ether synthesis involves the reaction of an alkoxide or phenoxide ion with an alkyl halide.$(i)$ Phenol

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$i$ only

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(A) The synthesis of ethers via the Williamson ether synthesis involves the reaction of an alkoxide or phenoxide ion with an alkyl halide.$(i)$ Phenol $(C_6H_5OH)$ reacts with $KNH_2$ to form potassium phenoxide $(C_6H_5OK)$. This phenoxide ion then undergoes an $S_N2$ reaction with propyl bromide $(CH_3CH_2CH_2Br)$ to yield phenyl propyl ether. This is a valid synthesis.(ii) Propanol $(CH_3CH_2CH_2OH)$ reacts with $NaOH$ to form sodium propoxide. However,the subsequent reaction with bromobenzene $(C_6H_5Br)$ does not occur because aryl halides are unreactive towards nucleophilic substitution under these conditions ($S_N2$ is not possible on an $sp^2$ hybridized carbon).(iii) Similarly,$NaH$ converts propanol to sodium propoxide,but the reaction with bromobenzene still fails for the same reason as in (ii).Therefore,only reaction $(i)$ will work.

The following are possible syntheses of phenyl propyl ether. Which one would work?
$(i)$ $C_6H_5OH$ $\xrightarrow{KNH_2}$ $\xrightarrow{CH_3CH_2CH_2Br}$
(ii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaOH}$ $\xrightarrow{C_6H_5Br}$
(iii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaH}$ $\xrightarrow{C_6H_5Br}$

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The following are possible syntheses of phenyl propyl ether. Which one would work?$(i)$ $C_6H_5OH$ $\xrightarrow{KNH_2}$ $\xrightarrow{CH_3CH_2CH_2Br}$(ii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaOH}$ $\xrightarrow{C_6H_5Br}$(iii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaH}$ $\xrightarrow{C_6H_5Br}$