The desired reaction scheme is therefore20.22(a)Ethanenitrile has the same number of carbon atoms as ethyl alcohol. This suggests a reactionscheme proceeding via an amide.The necessary amide is prepared from ethanol.(b)Propanenitrile may be prepared from ethyl alcohol by way of a nucleophilic substitution reac-tion of the corresponding bromide.20.23Step 1:Protonation of the nitrileStep 2:Nucleophilic addition of waterStep 3:Deprotonation of imino acidWaterOH2HydroniumionH3ONHRCHOHProtonated formof imino acidNHRCOHImino acidRCNHProtonated form of nitrileH2OWaterNHRCOH2Protonated formof imino acidH2OWaterHydroniumionHO
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