The Oxygen in HOCOO-: Does it Participate in Resonance?

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In summary, the oxygen in the OH group of HOCOO- has electron-withdrawing effects, but adding electrons to it would disrupt its current bond. Resonance structures can be drawn where the oxygen participates in resonance, but it is important to consider which resonance structure is the most important contributor to the overall resonance hybrid. Factors such as electronegativity and stability can help determine the importance of a resonance structure. This suggests that the particular resonance structure with a double bond to the central carbon may not be a major contributor to the overall structure of HOCOO-.
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MathewsMD
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For the molecule HOCOO-, does the oxygen in the OH group participate in resonance? Is that particular contributing structure a major contributor to the hybrid structure?

After a bit of discussion with peers, we agree the oxygen has electron-withdrawign effects, but since it is already bonded to a hydrogen, adding electrons to the oxygen would disrupt its current bond (i.e. too many electrons would destabilize the atom). Is there any support for the oxygen in the OH either participating or not participating in resonance? If so, do you mind providing an explanation? Thank you!
 
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You can certainly draw resonance structures where the oxygen in the OH group contains a double bond to the central carbon. However, you should also consider whether that resonance structure is an important contributor to the overall resonance hybrid. What factors do you know that help you determine which resonance structures are the most important to consider? (if you don't know, here's a good place to start: http://www.chem.ucla.edu/harding/tutorials/resonance/imp_res_str.html). What does this tell you about that particular resonance structure in comparison to the other resonance structures for HOCOO–?
 

1. What is HOCOO- and why is its oxygen important?

HOCOO- is a chemical compound with the formula HOOC-COO-. The oxygen in this compound is important because it is involved in several chemical reactions and plays a crucial role in the structure and properties of the molecule.

2. Does the oxygen in HOCOO- participate in resonance?

Yes, the oxygen in HOCOO- does participate in resonance. This means that the electrons in the molecule are delocalized and can move between different atoms, resulting in multiple possible structures for the molecule.

3. How does resonance affect the properties of HOCOO-?

Resonance in HOCOO- results in a more stable molecule with a lower energy state. This can affect the molecule's reactivity and its ability to form bonds with other atoms.

4. Is the oxygen in HOCOO- more electronegative than other atoms in the molecule?

Yes, oxygen is more electronegative than other atoms in HOCOO-. This means that it has a stronger attraction for electrons and will pull them closer to itself, contributing to the molecule's polarity and reactivity.

5. Can the oxygen in HOCOO- form hydrogen bonds?

Yes, the oxygen in HOCOO- can form hydrogen bonds with other molecules or atoms that have a hydrogen atom bonded to an electronegative atom, such as nitrogen or oxygen. This can affect the molecule's solubility and interactions with other substances.

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