The influence of water on cyanide displacement of 1-halobutanes using 18-crown-6 ether as phase transfer catalyst

The influence of water on the cyanide displacement reaction of 1-chlorobutane and of 1-bromobutane has been studied. Kinetics of both reactions have been followed under homogeneous and transfer conditions. The influence of water on the reaction rate and on the relative molar conductivity of the 18-crown-6 ether-KCN complex has been measured. In the first reaction, water reduces the reactivity of cyanide anions by solvating them. In the second reaction, this negative effect is overcompensated by the positive influence of water on the transfer steps between solid and liquid phases.