
TY  - JOUR
A1  - Anderson, RJ 
A1  - Ang, P 
A1  - England, BD 
A1  - McCann, VH 
A1  - McLennan, DJ 
T1  - Solvent effects on the rates of miscellaneous nucleophile-promoted reactions in aqueous-alcoholic solvent mixtures
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1969
VL  - 22
IS  - 7
SP  - 1427
EP  - 1437
KW  - 
UR  - https://doi.org/10.1071/CH9691427 
N2  - 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. 
ER  -

