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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: trainee on October 16, 2017, 08:17:11 PM

Title: What's NH3 as a leaving group?
Post by: trainee on October 16, 2017, 08:17:11 PM
I thought NH3 would be a terrible leaving group because it's so basic but apparently it's a better leaving group than water. Can someone clear this up? I was holding the pka values as guidelines with lower pka = better LG
Title: Re: What's NH3 as a leaving group?
Post by: Babcock_Hall on October 16, 2017, 09:14:10 PM
Both species are polyprotic, and one should specify which protonation state (and which pKa) one means IMO.
Title: Re: What's NH3 as a leaving group?
Post by: Enthalpy on October 17, 2017, 09:32:42 AM
Could his relate with the C-N bond being weaker than C-O?

kJ/mol
391   HO-C2H5
352   H2N-C2H5