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Ochem 2012 Review Guides.pdf


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Miscellaneous
Nucleophiles and Electrophiles
Most strong nucleophiles have a negative charge (must have lone pairs of electrons)

Nucleophile Strength
in Aprotic Solvents

Nucleophile Strength
in Protic Solvents

C N OF
Cl
Br
I

C N OF
Cl
Br
I

Common Electrophiles

R2

O
R

X

R

R'

R1

R3

Reaction intermediates (carbocations, radicals, carbanions)
Carbocation Stability
Radical Stability
Carbanion Stability
3 > 2 > 1 > Me
3 > 2 > 1 > Me
Me > 1 > 2 > 3
Resonance Stabilization (electron delocalization)
Inductive Effects
Oxidation/Reduction Rxns (Identifying)
Degrees of Unsaturation (CNH2N+2)

Ranking Acids and Bases
1) Charge - More negatively charged species are typically more basic, and more positively charged species
are typically more acidic.
2) Atom - The larger and/or more electronegative the atom with a negative charge, the more stable it is.
3) Resonance stabilization.
4) Dipole Induction - Electron withdrawing groups (i.e., electronegative atoms) near the atom that has the
negative charge stabilize the ion/molecule.
5) Orbitals – a pair of electrons is more stable as follows: sp > sp2 > sp3

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