
%0 Journal Article
%A Anderson, RJ 
%A Ang, P 
%A England, BD 
%A McCann, VH 
%A McLennan, DJ 
%T Solvent effects on the rates of miscellaneous nucleophile-promoted reactions in aqueous-alcoholic solvent mixtures
%J Australian Journal of Chemistry
%D 1969/07/01
%V 22
%N 7
%P 1427-1437
%K 
%R https://doi.org/10.1071/CH9691427
%U https://www.publish.csiro.au/paper/CH9691427 
%X The rates of E2 elimination from DDT and SN2 substitution on allyl bromide by alkoxide and hydroxide ions have been measured using aqueous-alcoholic solvent mixtures. The results are anomalous in terms of previous theories. The E2 hydrogen nucleophilicity order of OEt- > OMe- > OH- towards 2-phenethyl bromide in dioxan has been obtained by extrapolating rates of reaction in alkaline dioxan-alcohol or dioxan-water mixtures to 100% dioxan. The nucleophilicity order contrasts with the basicity order: OEt- > OH- > OMe- but is the same as the carbon nucleophilicity order. The validity is questioned of using similar carbon- nucleophilicity and elimination-reactivity orders as positive evidence for the E2C mechanism of eliminations promoted by weak bases which are also strong carbon nucleophiles. 
