Ch_322b_18.16

Ch_322b_18.16 - Nitriles This synthesis is an alternative...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Nitriles This synthesis is an alternative to the reaction of an alkyl halide with cyanide ion, which proceeds by an S N 2 mechanism. One standard way of preparing a nitrile is by the dehydration of the corresponding primary amide with reagents such as P 4 O 10 (called phosphorous pentoxide , P 2 O 5 ) or refluxing acetic anhydride . CH 3 CH 2 CNH 2 O = propionamide P 2 O 5 85 o C CH 3 CH 2 C N (-H 2 O) propanenitrile Hydrolysis of Nitriles Nitriles are considered derivatives of carboxylic acids because hydrolysis of a nitrile produces an acid. As with amides, the rate of hydrolysis is faster under either acidic or basic conditions than at neutral pH. R-C N H 3 O + H 2 O heat HO- H 2 O heat RCO 2 H + NH 4 + RCO 2- + NH 3 A Mechanism for the Acidic Hydrolysis of Nitriles The nitrile is a polar functional group similar to a carbonyl: R-C N: R-C=N: : +- R-C N: ! + !" polarization of charge in the nitrile function Stage 1: hydrolysis of nitrile to amide protonation of the nitrile R-C N: + H-O-H...
View Full Document

This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

Page1 / 6

Ch_322b_18.16 - Nitriles This synthesis is an alternative...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online