Choose the best synthesis of phenyl n-propyl | vedclass

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Question

(A) The synthesis of phenyl $n$-propyl ether is best achieved via the Williamson ether synthesis,which involves the reaction of a phenoxide ion with a

Vedclass · Accepted Answer

Phenol + $Na$ metal followed by $CH_3CH_2CH_2Br$ in a polar aprotic solvent.

Vedclass · Answer

(A) The synthesis of phenyl $n$-propyl ether is best achieved via the Williamson ether synthesis,which involves the reaction of a phenoxide ion with a primary alkyl halide. $(a)$ Phenol reacts with $Na$ metal to form sodium phenoxide $(PhO^-Na^+)$. This nucleophilic phenoxide ion then undergoes an $S_N2$ reaction with $n$-propyl bromide $(CH_3CH_2CH_2Br)$ in a polar aprotic solvent to yield phenyl $n$-propyl ether. This is the correct method. $(b)$ This reaction would require an $S_N2$ attack on bromobenzene,which is not possible because the $C-Br$ bond has partial double-bond character due to resonance,making it resistant to nucleophilic substitution. $(c)$ Anisole does not react with $Na$ metal. $(d)$ This reaction does not produce the desired ether; it would likely result in no reaction or side reactions.

Choose the best synthesis of phenyl $n$-propyl ether.

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