A nitrile is any organic compound that has a. alkyl halides undergo nucleophilic aliphatic substitution with alkali metal cyanides in the Kolbe nitrile synthesis. Amide to Nitrile Reduction;. Synthesis of Nitriles. Table of Contents. Nitriles are formed by an SN2 reaction between a bromide and sodium cyanide; Kolbe Nitrile Synthesis. Nucleophilic Substitution (S N 1 S N 2) Nucleophilic substitution is the reaction of an electron pair donor (the nucleophile, Nu). The Kolbe nitrile synthesis is a method for the preparation of alkyl nitriles by reaction of the corresponding alkylhalide with a metal cyanide. With this background, we can look back at the restriction that our examples of S N 2 reactions (nitrile and ether synthesis) only work well on primary alkyl halides. Want to watch this again later? Sign in to add this video to a playlist. Bimolecular Nucleophilic Substitution (SN2) Reaction THE NUCLEOPHILIC SUBSTITUTION REACTIONS BETWEEN HALOGENOALKANES AND CYANIDE IONS. the halogen is replaced by a -CN group and a nitrile is produced. Kolbe Nitrile Synthesis. The reaction of primary aliphatic halides and alkali metal cyanides - the Kolbe Nitrile Synthesis - gives nitriles in good yields. In the Kolbe nitrile synthesis, why is that when we use AgCN in diethyl ether solvent for reacting with RX, the process involves a SN1 mechanism instead of SN2? Synthesis of Amines I. Amine Alkylation by SN2 reaction Amines can be alkylated in SN2 fashion by alkyl halides; primary halides are best for this.