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I was reading a book on organic chemistry by David Klein and I came across this question, but I wasn't able to understand why one amine is more acidic than the other.

acidity on amines

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Have you taken into account that there is a $\ce{-CH3}$ group attached to the top N which has +I effect i.e., electron donating effect?

$\ce{-CH3}$ group will destabilize the negative charge on N formed after the release of proton.

Electron releasing group decreases acidic strength of a compound. So in this question proton of primary amine is more acidic and that of secondary amine is less acidic.

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  • $\begingroup$ I suppose it is too much of a hint to fully draw out the -CH3 group. I guess the intent of the question is to see who takes the time to visually analyze and digest the question. Or else the instructor has not made it clear that a line is shorthand for -CH3. $\endgroup$ May 16, 2021 at 13:49

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