Chemistry Penicillin Structure: Acidic, Neutral or Basic?

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Penicillin is expected to be acidic due to the presence of the carboxylic acid group (-COOH). The nitrogen atom in the structure, while potentially basic, is influenced by the adjacent carbonyl group (=C=O), which reduces its ability to accept protons. This deactivation of the nitrogen's electron density further supports the acidic nature of penicillin. The discussion confirms the reasoning behind this classification, highlighting the structural influences on acidity and basicity. Overall, the analysis concludes that penicillin is primarily acidic.
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Homework Statement



"Penicillin"[/URL]

From the structure of penicillin above, would you expect it to be acidic, neutral or basic? Explain your answer as fully as you can.

[h2]Homework Equations[/h2]
[h2]The Attempt at a Solution[/h2]

I think it would be acidic because of the -COOH. The -NH- can be basic, but it is attached to =C=O which is deactivating. the electron density on the N atom is reduced and the tendency to accept a proton decreases.

The other Nitrogen atom is also bonded to a deactivating =C=O.

Is this reasoning ok?

thnks
 
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You got it.
 
nice... thnks
 
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