2+ Year Member
Jul 31, 2015

So with my DAT coming up next week (yikes!), I'm trying to fill in all the gaps in my knowledge.

I'm a little confused about hydrogen acidity after having done a question on DAT Bootcamp in which the most acidic H on a compound was a H off a carbon on a triple bond (sp hybridized). After reading the explanation given, I got that:

H on sp hybridized carbons > H on sp2 > H on sp3 is terms of acidity because greater s character makes it more stable.
However, I read somewhere that vinylic H have a pka of I am very confused as to how H on sp2 could be more acidic than a H on sp3...Any help would be greatly appreciated.