Which Acetylide Anion and Alkyl Halide Can Form CH3C≡CCH2CH2CH2CH3?

[MarcL]

I was having "trouble" with a question: What acetylide anion and alkyl halide can be used to prepare each alkyne? Indicate all possibilities when more than one route will work
CH₃C≡CCH₂CH₂CH₂CH₃

I know 2 possibilities... I can "cut" at the first methyl group and create a methyl halide + the nucleophile. OR I can "cut" at the triple bond ( right after... sorry for my terminology) to create the nucleophile + 1° alkyl halide.

My answer key doesn't say i can cut "further" in, like let's say at the 2nd CH2 or third, which is weird to me because all of them will be able to create a substitution reaction... no? :/

 

[Greg Bernhardt]

Thanks for the post! Sorry you aren't generating responses at the moment. Do you have any further information, come to any new conclusions or is it possible to reword the post?

 

[PhaseShifter]

It's simpler than you think. Look at the original question, and tell me the definition for "acetylide ion."