MadSci Network: Chemistry |
Dilute HCl is not going to give you nucleophilic substitution, especially on a primary alcohol such as the ones you list, at any rate you need to worry about in a titration. As a matter of fact it shouldn't react *very* quickly even with a tertiary alcohol -- it will react with strong (hydroxide) bases first. The technique is simply to reach your endpoint fairly quickly, and then stop, even if after several minutes the solution turns clear again. This will eliminate false-negative results stemming from competing reactions, which take longer than simple acid-base reactions. Incidentally, you see the same phenomenon (gradual fading of the pink endpoint color) even in titrations in which no alcohol is present, if the mixture is exposed to air. The reason is that the base (you need fairly high pH, about 9, for phenolphthalein to turn pink) reacts with CO2 from the air to form carbonate. Dan Berger MadSci Administrator
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