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 acid11WaterOH2HydroniumionH3O1NHRCHOH1Protonated formof imino acidNHRCOHImino acid1RCNHProtonated form of nitrile1H2OWaterNHRCOH21Protonated formof imino acid1H2OWaterHydroniumion
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.