substitution and elimination reactions - orgo 1

3 polar protic solvents

water, ethanol, isopropanol

polar aprotic solvents

acetone, acetonitril, DMSO, DMF

strong nucleophiles (8)

I-, SH-,CN-, OH-, (CH3CH2)2NH, CH3O-, (CH3CH2)3P

what are the four things that make a nucelophile strong

• -q

• larger + very polarizable

• not very electronegative

• does not have bulky (alkyl) gRs on it (blocks it ability to get close to E+)

rank the stability of charged intermediates (carbocations)

• mehtyl cation

• primary cation

• benzyl cation

• allyl cation

• tertiary cation

• secondary cation

• vinyl cation

weak nucleophiles

F- (very dense and not polarizable, very EN), H2O, (CH3)2O

moderate nucelophiles

Br-, NH3, (CH3)2S, Cl-, (CH3)COO-

good leaving groups

halogens, sulfate, sulfonate (e.g mesylate OMs, Tosylate Ots), water, amines (R3N), sulfides (R2S) or anything that is stable (CB of a WA)

strong bases

h-, nh2-

weak bases

dbu, dbn

strong nu/b

ho-, ch3o-, ch3ch2o-, tert-butoxide