Leaving Groups, Solvents, Nucleophiles, and Bases

nonpolar solvents

alkanes, cycloalkanes, toluene, benzene, ether.

Mediocre Bases

RNH2, Na2CO3

Great Leaving Groups

I, Br, Cl- OTs, OCF3, OMs, and H2O (not OH).

polar aprotic solvents

DMF, DMSO, acetonitrile, acetone, ethyl acetate and nitromethane

. . These are species that can donate an electron pair to form a new covalent bond.

Very Strong Bases

NH2, H, HC≡C-

weak bases

NH3, CN, RCOOH, Cl, Br, 1, NaHCO3

Strong Bases

RO, HO

leaving groups

These are groups that can depart with a pair of electrons to form a stable species

Mediocre Leaving Groups

: F, CH3COO, NH3 (not NH2).

Bad Leaving Groups

OH, OCH3, NH2

polar protic Solvents

Acetic acid, H2O, ROH, NH3•.

VERY GOOD Nucleophiles

F, HS, RS-.

Good Nucleophiles

: Br, HO, RO, CN, N3-.

fair nucleophiles

NH, Cl, F, RCO.

Weak nucleophiles

H2O, ROH

very weak nucleophiles

RCO2H

are alchohols strong or weak nu?

weak

is water a strong or weak nu

weak

tertBuO-

E2 reactions
bulky and nonnucleophillic

DBN

E2 reactions
bulky and nonnucleophillic

DBU

E2 reactions
bulky and nonnucleophillic