Chemical Forums
Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: confusedstud on May 04, 2015, 09:46:17 AM
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My lecturer said that the C=O on the ketone has 2 electron donating groups while the C=O on the ester only has one electron donating group and the -OR group a withdrawing group. And this causes the ketone to be a better HBA than the ester.
However, isn't the -OR group also electron donating in fact even more electron donating? So shouldn't the reason for the ester being a poorer HBA be because the 2 electron donating groups from the ester are stronger than the 2 from the ketone. As a result the C from the C=O of the ester is more negatively charged compared to the C from the C=O of the ketone. Because of that, the ester's =O cannot pull the electron density from the C as effectively as the ketone's =O which makes the ketone's =O a better HBA?