So in the reaction shown in the link below, it takes a longer time for the primary OH group to be protected with NsCl (2hr?) than the TsCl (1hr) group protects the secondary OH group. Can anyone offer a reason why this is so?
http://en.wikipedia.org/wiki/File:TolterodineSynthesis.png
Apparently, the NsCl and TsCl (both sulfonates) can differentially select between the primary and secondary OH group of this diol by exploiting the differences between the acidity of the alcohol groups. (Acidity of an alcohol: primary> secondary> tertiary)
http://en.wikipedia.org/wiki/File:TolterodineSynthesis.png
Apparently, the NsCl and TsCl (both sulfonates) can differentially select between the primary and secondary OH group of this diol by exploiting the differences between the acidity of the alcohol groups. (Acidity of an alcohol: primary> secondary> tertiary)