| 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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