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srraghav1542
Joined: 03 Mar 2008
Posts: 11
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 Posted: Mon Mar 10, 2008 7:05 pm Post subject: Quick Question regarding nucleophiles |
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| I came across a question on the biological sciences GS#2 regarding the basicity (nucleophilicity) of the amino and carboxl group of an Amino Acid. Under basic conditions, the carboxyl group would be COO- and the amino group would be NH2. Why would NH2 be more likely to protonate than COO-. If someone could clarify this that would be great. Thanks |
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mcat_premed3832
Joined: 19 Oct 2006
Posts: 412
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| Posted: Mon Mar 10, 2008 8:19 pm Post subject: |
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The short answer: -COO- (the carboxylate anion) is resonance stabilized.
The longer answer: don't forget that -COOH (carboxylic acid functional group) is by definition an acid and therefore a proton donor.
On the other hand, the amino group -NH2 can act as a base and thus, by definition, a proton acceptor. |
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