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Q. How many of the given reaction will form tert-Butyl ethyl ether
(I) tert - Butanol + Ethanol $\xrightarrow{H^{+} }$
(II) tert-Butyl bromide + Sodium ethoxide $\to$
(III) Sodium tert-butoxide + Ethyl bromide $\to$
(IV) Isobutene + Ethanol $\xrightarrow{H^{+} }$

Alcohols Phenols and Ethers

Solution:

$(CH_{3})_{3}CBr+NaOC_{2}H_{5}$ can ’t be applied for synthesising the ether because sod. ethoxide, being a strong base, will preferentially cause elimination reaction
$(CH_{3})_{3}CBr \xrightarrow{ {}^{-}OC_{2}H_{5} }(CH_{3})_{2}C = CH_{2}+HBr$
Rest other forms tert-Butyl ethyl ether