why-the-following-sn2-reaction-of-1-bromide-by-alkynide-fails-to-give-the-desire

Question

Why does the following S_N2 reaction of a 1° bromide by alkynide fail to give the desired product?

SN2 reaction diagram showing failure to form product due to poor leaving group and acidic proton.

Accepted Answer

Due to the presence of an acidic alcoholic proton in the substrate, an acid-base reaction will occur instead of a substitution reaction.

Answer

Due to the presence of a poor leaving group, a substitution reaction will not occur.

Answer

Due to the presence of an aprotic solvent, an S_N2 reaction is not feasible.

Answer

None of these.