Which would react faster with MeI in aqueous solution: OH- or Et3N?
I know that the reaction in aqueous solution would be an Sn1 reaction and so steric hindrance wouldn't have such a great effect. I am not sure which is a better nucleophile out of OH- and Et3N. OH- is charged, but the Et groups on Et3N are electron donating and would increase the availability of the lone pair on N. Also O is small than N and more electronegative, but I don't know if that would affect nuceophilicity.
The last one may be the best.
http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch08/ch8-5.html
http://chem.pdx.edu/~wamserc/C334F98/8notes.htm
http://books.google.com/books?id=mXFYSre-dLgC&pg=PA131&lpg=PA131&dq=rank+nucleophiles&source=bl&ots=xFJmnm7_Kn&sig=oP_XkE8_ZTsWZI4h6mo8S6YC83s&hl=en&ei=fEEcStXqLJPBtwe5l5nlCg&sa=X&oi=book_result&ct=result&resnum=4#PPA132,M1