Question

Which of the following reagents will deprotonate an alkylthiol(RSH) completely at equilibrium? Select all that apply. a. NaCN b, H20 c. NH3 d. NaNH2 e. NaO2CCHs

Our instructor said that if the pKa is >16 a reagent should completely deprotonate an alkylthiol. But he also said the pKa difference has to be at least 5, preferably 10, to completely deprotonate.

I'm not sure what pKa to use for some of these since they're sodium based-NaCN in particular. (And the pKa for a generic alkylthiol.

I think these are right:

H20=15.8 so no.

NH3=38 so yes

NaNH2=38 so yes

NaO2CCH3=24 so yes (?) its the conjugate base of a weak acid

NaCN I'm not sure. Ditto for water.

Answer 1