教学课件学术资源columbia大学有机化学课件20.html.pptxVIP

20.18Preparation of Nitriles;nucleophilic substitution by cyanide onalkyl halides (Sections 8.1 and 8.13) cyanohydrin formation (Section 17.7) dehydration of amides;Example;Example;uses the reagent P4O10 (often written as P2O5);20.19Hydrolysis of Nitriles;Hydrolysis of Nitriles;Hydrolysis of Nitriles;Example: Acid Hydrolysis;Example: Basic Hydrolysis; Hydrolysis of nitriles proceeds via thecorresponding amide. We already know the mechanism of amidehydrolysis. Therefore, all we need to do is to see how  amides are formed from nitriles under the  conditions of hydrolysis.; The mechanism of amide formation is analogousto that of conversion of alkynes to ketones. It begins with the addition of water across thecarbon-nitrogen triple bond. The product of this addition is the nitrogen analog of an enol. It is transformed to an amideunder the reaction conditions.;Step 1;Step 1;Step 2;Step 2;Step 3;Step 3;Step 4;N;20.20Addition of Grignard Reagentsto Nitriles; Grignard reagents add to carbon-nitrogen triplebonds in the same way that they add to carbon-oxygen double bonds. The product of the reaction is an imine.;Addition of Grignard Reagents to Nitriles;Example