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April 21, 2014

Homework Help: Relative Acidities

Posted by Allie on Wednesday, February 16, 2011 at 7:24pm.

Rank the given compounds on their relative acidity.

Here was the order I thought it was but it turned out to be wrong. (i based it based off of sp being most acidic and sp3 being least acidic)

STRONGEST
HC(triple bond)C-CH3
H2C=CH2
CH3NH2
H2O
CH4--> WEAKEST

and then I looked up the actual pka values and got the following order but it was still wrong...

HC(triple bond)C-CH3 --> STRONGEST
CH3NH2 pka 10.58
H20 pka 15.74
H2C=CH2 pka 44
Ch4 pka 50 ---> WEAKEST

please help I am really confused
Thanks :)

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