Which Is the Best Leaving Group: Cl-, Enolate, or NR3?

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SUMMARY

The discussion centers on evaluating the best leaving group among Cl-, enolate, and NR3. Participants conclude that Cl- is the superior leaving group due to its association with a strong acid (HCl), which results in a weak conjugate base. The resonance stabilization of the enolate is acknowledged, but it is ultimately deemed less effective than the leaving ability of Cl-. The consensus is that Cl- outperforms NR3 due to the relative acid strengths of their corresponding acids.

PREREQUISITES
  • Understanding of leaving groups in organic chemistry
  • Knowledge of acid-base strength and conjugate bases
  • Familiarity with resonance structures and their stability
  • Basic concepts of enolate formation and structure
NEXT STEPS
  • Study the properties of leaving groups in organic reactions
  • Learn about the strength of acids and their conjugate bases
  • Explore resonance stabilization in organic compounds
  • Investigate the formation and reactivity of enolates
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding the mechanisms of nucleophilic substitution reactions.

destinc
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which is the best leaving group?
Cl- enolate NR3


I couldn't figure out how to draw the enolate here, but it is a basic 3 carbon one.
I believe the answer is Cl because resonance on the enolate will disperse the neg. charge. Am I on the right track or is there a factor I am missing?
 
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destinc said:
which is the best leaving group?
Cl- enolate NR3


I couldn't figure out how to draw the enolate here, but it is a basic 3 carbon one.
I believe the answer is Cl because resonance on the enolate will disperse the neg. charge. Am I on the right track or is there a factor I am missing?

strong acid=> weak conjugate base(it is leaving group)=>good leaving group.
I don't know enolate looks like but out of other two Cl is best since it's acid(HCl) is stronger acid than that of NR3(that's NR3H)
 

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