|Chapter 8: Nucleophilic Substitution
- Unless the -OH group is converted into
a better leaving group, then alcohols are
poor substrates for substitution reactions.
- Protonation to convert the leaving group into H2O
has limited utility as not all substrates or nucleophiles can be utilised
under acidic conditions without unwanted side reactions.
- An alternative is to convert the alcohol into a tosylate,
which has a much better leaving group and will react with nucleophiles without
the need for the acid.