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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Winga on March 26, 2005, 07:07:29 AM

Title: Nucleophilic Substitution
Post by: Winga on March 26, 2005, 07:07:29 AM

Why weaker the base, better the leaving group?

Title: Re:Nucleophilic Substitution
Post by: Donaldson Tan on March 26, 2005, 07:23:25 AM

i would tend to think weaker base in the sense that it would be less reactive, thus indicate higher stability to act as a leaving group

Title: Re:Nucleophilic Substitution
Post by: dexangeles on March 27, 2005, 04:01:00 PM

less basic --> less nucleophilic --> better leaving group

Title: Re:Nucleophilic Substitution
Post by: Winga on March 27, 2005, 07:21:21 PM

But, less basic doesn't mean that it must be less nucleophilic, right?

Title: Re:Nucleophilic Substitution
Post by: Mitch on March 27, 2005, 07:29:13 PM

Maybe its because you don't want to encourage the competitive reaction of elimination.