4. (14 pts.) Propyne (3) is first treated with sodium amide (NaNH2) to generate a reactiventermediate 4, which is a carb

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4 14 Pts Propyne 3 Is First Treated With Sodium Amide Nanh2 To Generate A Reactiventermediate 4 Which Is A Carb 1 (99.23 KiB) Viewed 30 times

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 NH₂ (The conjugate acid of NH₂ is NH3, pKa = 35) 4 5 Br 6 (C10H10) (NaBr is a byproduct of this reaction)