Predict the order of acid strengths in the following series of cationic species: CH3CH2NH3 +, CH3CH=NH2

CH3CH=NH2+>CH3CH2NH3 +

Explanation:

There are certain structural features that determine the stability of cationic species. These features that lead to the stability and higher acid strength of cations are those features that stabilize the cation.

CH3CH=NH2+ is more acidic than CH3CH2NH3 + owing to the fact that CH3CH=NH2+ contains a double bond in close proximity with the hydrogen that can be lost as a proton. Electron withdrawal by the double bond (greater s character) makes it easier for this hydrogen to be lost as a proton compared to CH3CH2NH3 +.

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