Question

Predict the order of acid strengths in the following series of cationic

Answer 1

Answer:

CH3CH=NH2+>CH3CH2NH3+

Explanation:

A close examination of both structures will reveal that they are both amines hence they must have the polar N-H bond.

Electrons usually move towards the nitrogen atom and this makes both compounds acidic. We must also remember that some features of a compound may make it more acidic than another of close resemblance. Being more acidic may imply that the proton of the N-H is more easily lost.

CH3CH=NH2+ has an sp2 hybridized carbon atom in its structure which is known to be very electronegative due to increasing s character of the bond. It will withdraw electron density from the N-H bond thereby leading to a greater acidity of CH3CH=NH2+ in comparison to CH3CH2NH3+