ORGO 1 Nucleophiles/Bases

Examples of strong bases, but weak nucleophiles

NaH, DBN, DBU

Examples of strong bases and strong nucleophiles

OH-, OMe-, EtO-

Examples of weak bases, but strong nucleophiles

I-, Br-, Cl-, RS-, HS-, RSH-, H2S

Examples of weak bases and weak nucleophiles

H2O, MeOH, EtOH

If a reagent is a strong base and a weak nucleophile, what kind of reaction(s) will occur?

E2

If a reagnet is a strong base and a strong nucleophile, what kind of reaction(s) may occur?

SN2 and E2

If a reagent is a weak base and a strong nucleophile, what kind of reaction(s) may occur?

SN1 and SN2

If a reagent is a weak base and a weak nucleophile, what kind of reaction(s) may occur?

SN1 and E1

If an alpha carbon is primary, and the reagent is a strong base and a strong nucleophile, what kind of reaction(s) occur?

SN2 > E2

If the alpha carbon is primary, and the reagent is a weak base but a strong nucleophile, what kind of reaction(s) occur?

SN2

If an alpha carbon is secondary and the reagent is a strong base and a strong nucleophile, what kind of reaction(s) occur?

E2 > SN2

If the alpha carbon is tertiary and the reagent is a strong base and a strong nucleophile, what kind of reaction(s) occur?

E2

If an alpha carbon is either primary or secondary, and the reagent is a weak base but a strong nucleophile, what kind of reaction(s) occur?

SN2