[sweetbabu]

Please help me on following question.   

You are planning to carry out a reaction between propyne, CH3C≡CH and sodium amide, NaNH2.  You also need to choose an appropriate solvent for carrying out the reaction.  Would ethanol be suitable for this purpose?  Explain your rationale clearly.

[agrobert]

What do you think?  What do you know about alkyne reactivity/reactions?  Would ethanol interfere with NaNH₂?

[mir]

And what is it about the -:NH₂ ion?

[sweetbabu]

To form an propynylide anion completely with the base, a solvent should be weaker acid than propyne. That will exclude all alcohols.

Just as sodium amide deprotonates the propyne to give ammonia and the sodium salt of the propyne, any solvents that are more acidic than propyne will exchange the proton of the solvent to produce its anion and return propyne anion to propyne.
does it sound right???

[macman104]

Sounds like a pretty good explanation to me.

[agrobert]

To form an propynylide anion completely with the base, a solvent should be weaker acid than propyne. That will exclude all alcohols.

Just as sodium amide deprotonates the propyne to give ammonia and the sodium salt of the propyne, any solvents that are more acidic than propyne will exchange the proton of the solvent to produce its anion and return propyne anion to propyne.
does it sound right???

SO, what solvents can you use?  What is common for this reacton?