[FollowTheFez]

I'm a bit unsure of what's happening in this reaction. I have to give the product for the reaction attached.

I know that the answer is,



but I am unsure of how this happened and have no idea of where to start!
I'm not even too sure of what that first compound is. I first tried to do the reaction like that first compound was an acyl chloride but it didn't seem to work out.
Any hints?


Just looking at it a few hours later, it wouldn't be a nucleophilic substitution would it?

[Dan]

This is the synthesis of an alkyne from a vinyl halide.

Compare the formulas: C₈H₇Cl  C₈H₆

What has changed - has something been added/eliminated/substituted?

What kind of a reagent is NaNH₂ (acid/base/nucleophile/electrophile)?

[FollowTheFez]

This is the synthesis of an alkyne from a vinyl halide.

Compare the formulas: C₈H₇Cl  C₈H₆

What has changed - has something been added/eliminated/substituted?

What kind of a reagent is NaNH₂ (acid/base/nucleophile/electrophile)?

The Cl has been eliminated and and extra bond formed to make a triple bond.

NaNH₂ is basic isn't it?  I think I can just ignore the Na? Which would make the compound NH₂^-. Which would make it a nucleophile!

So would I push the electrons in the Cl-C bond onto Cl, and attack the resulting positive charge on the C atom with the nucleophile? But then that just makes an amine. I assume at this point the H₃O⁺ comes into it.

So at the moment I have



I don't think that's right. Have I gone wrong somewhere? That compound looks stable.
If I'm correct, I think that the H₃O⁺ would still react with the NH₂?

[Hunter2]

Its elimination not substitution. What else reaction can do NH₂^-?

[FollowTheFez]

Its elimination not substitution. What else reaction can do NH₂^-?

Whoops. Sorry. Well the NH₂ being basic can deprontonate stuff.  But I didn't think that applied here seeing as there was no hydrogen involved.