Nucleophilicity + Basicity

sn1, sn2, e1, e2

Nucleophilicty

kinetic phenomenon: how rapidly does the molecule add to an electrophile?

Nucleophilicity has high ___ and high ___

electron density, polarizability

Basicity

thermodynamic phenomenon: how stable is the base relative to the conjugate base of the acid?

Basicity has low ___ and __ negative charge/electron pair

Ka for conjugate acid, unstable

Strong Base/Weak Nucleophile

H^-, DBN, DBU

Strong Base/Strong Nucleophile

OH^-, MeO^-, EtO^-, ProO^-

Weak Base/Strong Nucleophile

I^-

Br^-

Cl^-

CN^-

RS^-

HS^-

RSH

H₂S

carboxylic acid

Weak Base/Weak Nucleophile

H₂O, MeOH, EtOH