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Why di-tertiary butyl ether cannot be pr...

Why di-tertiary butyl ether cannot be prepared byWilliamson’s synthesis ?

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To prepare tert-butyl ether by williamson synthesis. We require tert-butyl bromide and sodium tert-but-oxide. Since tert-butyl bromide is `3^@` alkyl lialide, it prefers to undergo elimination rather than substitution due to sterically hinderance structure. Therefore isobutylene is obtained as the product rather than tert butyl ether.
`underset("tert , butyl bromide")underset(CH_3)underset(|)overset(CH_3)overset(|)(CH_3-C-Br)+underset("Sodium tert butoxide")underset(CH_3)underset(|)overset(CH_3)overset(|)(Na^(+)O-CH_3)rarrunderset("Isobutylene")(CH_3-overset(CH_3)overset(|)C)=CH_2+underset(CH_3)underset(|)overset(CH_3)overset(|)C-OH`
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  • Williamson's synthesis of preparing dimethyl ether is a

    A
    `S_N1` reaction
    B
    electrophilic substitution reaction
    C
    `S_N2` reaction
    D
    electrophilic addition reaction

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