(Solved): 4. (14 pts.) Propyne (3) is first treated with sodium amide (NaNH2) to generate a reactiventermedi ...

4. (14 pts.) Propyne (3) is first treated with sodium amide (NaNH2) to generate a reactiventermediate 4, which is a carbanion. This first reaction is a Brønsted acid-Brønsted base reaction. Intermediate anion 4 is combined with benzyl bromide (5, shown below) to give product 6, having molecular formula C10H10. Determine the structures of 4 and 6 (some information about the relative pKa's is provided to help you). Draw arrow formalism for each step for full credit. H3C-CEC-H 3 pka > 40 Na pka = 25 NH? (The conjugate acid of NH? is NH3, pKa = 35) 4 5 Br 6 (C10H10) (NaBr is a byproduct of this reaction)