nnath

Thanks hypervalent_iodine. Makes sense.

With that picture, the question that was given to me was "which proton is more acidic?". I'm assuming they are referring to the H that is bonded to the carbon and the H that is bonded to the N. My answer is the H that is bonded to the N, but the correct answer is the H which is bonded to the carbon. I'm asking why is this the case?

Which proton is more acidic, the one on the left or right? My answer would be the proton attached to the N because N is more electronegative than the carbon that the circled H is attached to. I get that the negative charge on the conjugate base (after removing the H on the carbon) is found in an sp orbital, which stabilizes the negative charge more than an sp3 orbital, but isn't it more important that the proton is attached to the more electronegative atom? This question is taken from David Klein's Orgo as a Second Language book.