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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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    $\begingroup$ Have you been able to draw the structures of the conjugate bases? $\endgroup$ – airhuff Jan 18 '17 at 8:19
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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.

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  • $\begingroup$ 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. $\endgroup$ – narendra kumar Jan 18 '17 at 12:36
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    $\begingroup$ @narendrakumar that's what I meant $\endgroup$ – Resorcinol Jan 18 '17 at 14:24
  • $\begingroup$ Would the hydrogen have a donating effect due to the electronegativity difference between the nitrogen and the hydrogen? $\endgroup$ – Palash Taneja Jan 19 '17 at 8:31

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