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Charge Stability (Inductive effects (Electron-withdrawing groups…
Charge Stability
Inductive effects
Electron-withdrawing groups
Stabilize negative charges
De-stabilize positive charges
Electronegative groups are electron-withdrawing
Electron-donating groups
De-stabilize negative charges
Stabilize positive charges (i.e. carbocations)
Alkyl groups are electron-donating
Lose effectiveness with distance
Atom effects
Size
Bigger atoms can spread out a charge and make more stable
Electronegativity
More electronegative atoms can handle a negative charge better
Hybridization
Negative charge is more stable the greater the "s" character of an atom
"Charge is bad"
Unstable charges
Make for bad leaving groups
Make for unstable conjugate base
Stable charges
Make good leaving groups
Make for stable conjugate base
Resonance effects
Use resonance to spread a charge over multiple atoms