masterorganicchemistry.com
The pKa Table Is Your Friend
Why are pKas so important? Because every nucleophile is potentially a base, and vice versa. If you have a reaction where it looks like you might get SN2 or E2, look closely first - is there any chance of a simple acid-base reaction? For instance, take NaOH plus an alkyl thiol, R–SH. Is it an SN2? Or possibly an E2? Both are incorrect. The reaction that happens is the simplest one - deprotonation of SH, to provide water and the deprotonated thiol. Also, the pKa table tells you about leaving…
