2. We would like to use the phenylacetylide anion as a reagent in an SN2 reaction and we only
have three solvents available: methanol, acetone, and dimethylsulfoxide (DMSO). Of course, we
would like to ensure that our reagent will not react with the chosen solvent(s). Please complete
the three reactions below to show equilibrium arrows and products. Show the curved arrows and
necessary lone pairs for each forward and reverse reaction. Assign pKa values to the acids to
determine which side is favored (and adjust the equilibrium arrows accordingly). If the
difference in pK,'s exceeds 10 units please show only a "one way" arrow.
?
+
+
+
H-0
Below, please name the solvents (or solvent) that do not undergo any acid-base reaction with
phenylacetylide:
In terms of reactivity only, please briefly describe (less than 25 words, please) why the solvents
(or solvent) you named above would be suitable for "hosting" the reaction.
