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Organic Chemistry
Undergraduate 3
12/01/2017

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Term
If PKa of conjugate acid is 11 or greater,
Definition
basicity is greater than nucleophilicity
Term
If PKa of conjugate acid is 11 or less,
Definition
nucleophilicity wins over basicity
Term
conjugate acid: CH4, CH2=CH2, HC(triplebond)CH, NH3
Definition
Basic (way over 11)
Term
conjugate acid: CH3OH, H2O,
Definition
Basic (just over 11)
Term
conjugate acid: CH3SH, NH4+, HCN, H2S
Definition
nucleophilic (just under 11)
Term
conjugate acid: HN3, CH3OOH, H3O+, R-OH2+
Definition
Nucleophilic (just under 11)
Term
conjugate acid: HF, HCl, HBr, HI
Definition
Nucleophilic (way under 11)
Term
conjugate acid: CF3SO3H
Definition
Nucleophilic (way under 11)
Term
Good Nu/ Weak Base (Nu>B)
Definition
I-, Br-
SH-, RS- (e.g. CH3S-)
CN-, N3-
PPh3, PH2-
Term
Moderate Nu/ Weak Base (Nu>B)
Definition
Cl-, F-
RCOO- (e.g. CH3COO-)
RSH (e.g. CH3SH)
Term
Strong Nu/ Strong B (Nu>B)
Definition
R- (e.g. CH3-)
HC---C-, R-C---C-, NH2-
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