Why does the + sign move to O in the addition of alkene with water?

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SUMMARY

The discussion centers on the movement of the positive charge to the oxygen atom during the addition of water (H2O) to an alkene. Participants clarify that the oxygen atom, initially neutral with two lone pairs, becomes electron deficient after donating one lone pair to the carbocation (C+). This results in a formal charge calculation that reveals the oxygen's new positive charge. Understanding formal charge calculations is crucial for accurately interpreting molecular interactions in organic chemistry.

PREREQUISITES
  • Understanding of carbocations and their stability in organic chemistry.
  • Knowledge of formal charge calculations and their significance.
  • Familiarity with the structure and bonding of water (H2O).
  • Basic principles of electron donation and electron deficiency in chemical reactions.
NEXT STEPS
  • Study the mechanism of electrophilic addition reactions in alkenes.
  • Learn about the role of lone pairs in molecular interactions and charge distribution.
  • Explore advanced formal charge calculation techniques for complex molecules.
  • Investigate the concept of resonance and its impact on charge stability in organic compounds.
USEFUL FOR

Chemistry students, organic chemists, and educators seeking to deepen their understanding of reaction mechanisms and formal charge implications in organic reactions.

kelvin macks
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Homework Statement



my question is at part 2 , since c form ch3ch2 is electron deficient, but after OH2 added in , with lone pair electron on O, the c should be no longer electron deficient anymore. am i right? why the + sign is moved to O now?

Homework Equations





The Attempt at a Solution

 

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Please calculate the formal charge on oxygen. Remember that H2O has two lone electron pairs.
 
ChiralWaltz said:
Please calculate the formal charge on oxygen. Remember that H2O has two lone electron pairs.

do u mean now the O become electron deficient, since one lone pair of lectron is donated to C+, and now there's one lone pair left one the O atom?
 
Why is oxygen electron deficient at this point? How many valence electrons should it have to be neutral? How many to be positive? How many to be negative? Do all atoms have the same requirements for their valence shells?

Hint: this deals with the calculation of its Formal Charge…
 
kelvin macks said:
do u mean now the O become electron deficient, since one lone pair of lectron is donated to C+, and now there's one lone pair left one the O atom?

That is not what I said but it is another, less formal, way of looking at the same thing. Knowing how to calculate formal charges is good because books and people can make mistakes. Keeping track of your electrons is incredibly important in O Chem. Once you have seen an oxygen with three sigma bonds and a lone electron pair 100 times, you probably won't need to run the formal charge calculations because you know it is positive.

I prefer to know why rather than rely on memorizing though. The memorization is simply a byproduct.
 

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