Donating e- to electrophile makes it a better leaving group?

[libraryismyhome]

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Does donating electron density to electron withdrawing group or electrophile weakens and lengthens the bond so it becomes a better leaving group?

But I thought giving e- to electrophile weakens the electron withdrawing capability or electrophilic strength, so that it becomes a worse leaving group... 😕

 

[jwalla57]

do you have a particular example? dont completely understand.