Which would you expect to be the stronger acid?
a) B-chloroethyl or ethyl alcohol?
b) isopropyl alcohol or hexafluroisopropyl alcohol?
c) n-propyl alcohol or glycerol, HOCH2CHOHCH2OH?(2 should be subscripts)
d) Which alcohol of each pair would you expect to be the stronger nucleophile?
Generally speaking, alcohols with highly electronegative atoms attached (such as chlorine and fluorine) are much more acidic than their corresponding simple alcohols. Why is this? It is due to the inductive effect. It is the result of the electron-withdrawing effect of the electronegative atom which, in the un-ionized alcohol, decreases the electron density of the alpha carbon. The result is a high-energy structure with adjacent positive charges on the alpha and beta carbons. On the other hand, the presence of the halide reduces the energy of the anion since the negative charge on the oxygen can be dispersed by the nearby partially positive charge on the beta ...
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