ethyne vs Nh3 pka

[Faux]

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I'm looking at qvualt 8 question 14.


I would think that NH3 would be a weaker base/stronger acid than ethyne due to the rules chad mention? Doesn't the nitrogen stabilize the negative charge more than carbon? If so, how is this reaction more favorable if you want weaker products?

 

[HdK]

what's the answer? does it say NH3 is the weaker acid?

 

[Faux]

what's the answer? does it say NH3 is the weaker acid?

Yes and the reaction is favorable towards products.

 

[HdK]

yea...according to CARDIO, Nh3 should be the better acid..anyone?

 

[Dotoday]

No NH4+ is a stronger acid, not NH3. Ammonia is a stronger base than ethyne, and therefore can deprotonate ethyne. Ethyne has an sp hybridization and therefore makes a stronger ion. Thus is it a stronger acid.
Hope this helps.

Sent from my SPH-L710 using Tapatalk

 

[Faux]

No NH4+ is a stronger acid, not NH3. Ammonia is a stronger base than ethyne, and therefore can deprotonate ethyne. Ethyne has an sp hybridization and therefore makes a stronger ion. Thus is it a stronger acid.
Hope this helps.

Sent from my SPH-L710 using Tapatalk

Doesn't basicity increase going up and to the left? or is this just one of those exceptions?