why-alkynide-alkylation-reaction-shown-below-fails-to-yield-the-desired-product-

Question

Why alkynide alkylation reaction shown below fails to yield the desired product? What actual major product would be formed in this reaction?

Reaction scheme showing alkynide synthesis with alkyl halide and NaNH2.

Accepted Answer

Because the alkyl halide used in this reaction is hindered, an elimination reaction will occur instead of a substitution.

Structure of a substituted alkene with a chlorine leaving group.

Answer

Because the alkyl halide used in this reaction is hindered, an S_N1 reaction will occur instead of an S_N2 reaction.

Structure of a hindered alkyl halide with a chlorine leaving group.

Answer

Because of the use of a weak base, alkynide ions will not be formed for the desired substitution.

Structure of an alkynide with a chlorine leaving group.

Answer

Because of the presence of a poor leaving group, a substitution reaction is not possible.

Structure of a substituted alkene without a leaving group.