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

[destinc]

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?

 

[vkash]

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)