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Dolbier HW Solutions 455 - 549 CARBOXYLIC ACID DERIVATIVES...

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The desired reaction scheme is therefore 20.22 ( a ) Ethanenitrile has the same number of carbon atoms as ethyl alcohol. This suggests a reaction scheme 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. 20.23 Step 1: Protonation of the nitrile Step 2: Nucleophilic addition of water Step 3: Deprotonation of imino acid Water OH 2 Hydronium ion H 3 O NH RC HO H Protonated form of imino acid NH RC OH Imino acid RC NH Protonated form of nitrile H 2 O Water NH RC OH 2 Protonated form of imino acid H 2 O Water Hydronium ion H O
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