Wednesday, 30 March 2016

organic chemistry - What is the hybridization of the carbonyl oxygen in a carboxylic acid?


My professor sent out a review guide. One of the questions on this guide is



The carboxylic acid carbonyl oxygen is:

1. spX2
2. spX3
3. H-bond donor
4. rapidly equilibrating between spX3 and spX2
5. 1 and 3
6. 1 and 4



I chose (4) because of the resonance that can be drawn with a negative oxygen and positive carbon. However apparently the answer is (6). I don't understand how something can be equilibrating between two states and still be one of those states.


Could anyone explain?




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