Are Carbon-Oxygen Double Bonds More Stable Than Single Bonds?

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SUMMARY

Carbon-oxygen double bonds (C=O) exhibit greater thermodynamic stability compared to carbon-oxygen single bonds (C-O) due to the increased overlap of p-orbitals, leading to stronger π-bonds. In contrast, hydroxide (-OH) is not an effective leaving group in basic conditions, as it requires protonation to facilitate departure, which contradicts the nature of basic environments. The discussion highlights the importance of understanding bond stability and leaving group ability in organic chemistry reactions.

PREREQUISITES
  • Understanding of organic chemistry concepts, specifically bond types and stability.
  • Familiarity with thermodynamic principles related to chemical bonds.
  • Knowledge of reaction mechanisms, particularly in basic conditions.
  • Experience with functional groups and their reactivity in organic reactions.
NEXT STEPS
  • Research the thermodynamic principles governing bond stability in organic compounds.
  • Study the role of leaving groups in various reaction mechanisms, focusing on conditions that enhance their effectiveness.
  • Explore the concept of protonation and its implications for leaving group behavior in acidic versus basic environments.
  • Investigate the stability and reactivity of different functional groups in organic chemistry.
USEFUL FOR

Organic chemistry students, researchers in chemical sciences, and professionals involved in synthetic organic chemistry who seek to deepen their understanding of bond stability and reaction mechanisms.

SublimeGD
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2 quick ochem questions...

1. Why is a carbon oxygen double bond more thermodynamically stable than a carbon oxygen single bond?

2. Can -OH be a leaving group in basic conditions, it would seem strange to protinate it in basic conditions?

Thanks!
 
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SublimeGD said:
2 quick ochem questions...

1. Why is a carbon oxygen double bond more thermodynamically stable than a carbon oxygen single bond?

2. Can -OH be a leaving group in basic conditions, it would seem strange to protinate it in basic conditions?

Thanks!

More thermodynamically stable than what? Than RRC+-O-? Or R-CH2-OH?

OH is never a good leaving group unless the negative charge is somehow dealt with. In what base catalyzed reaction do you see OH- as a leaving group?
 

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