Which proton is more acidic... Vinylic or Allylic?

[BrazilianRider]

I dunno if this matters, but it popped up in my head and I didn't know the answer.

I'm leaning towards Allylic, but I honestly don't know, and it's why I'm asking you guys!

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[pilotdentist]

Allylic is my guess because i think it's resonance stabilized. More stable = more acidic.

 

[Triflate]

allylic - the conjugate base would be delocalized through the conjugated pi system, stabilizing it. this increases the acidity of an allylic proton. Vinyl halides have a pka of around 44 (depending on the groups attached to the alkene), so yeah, not acidic at all

 

[BrazilianRider]

Vinyl halides have a pka of around 44 (depending on the groups attached to the alkene), so yeah, not acidic at all

Holy **** lol... Thanks guys!

 

[Triflate]

oops sorry i didn't mean to say vinyl halides - i meant to say vinyl protons have a pka of around 44 - but anyway glad it helped!