Miscellaneous Reagents

rayagofu's version from 2015-07-05 00:05


Question Answer
OsO4osmium tetroxide - for dihydroxylation
Pb(OAc)4lead tetraacetate - for cleavage of diols
mCPBAmeta chloro perbenzoic acid - for epoxidations, and Baeyer villiger rxns of ketones
NaIO4sodium periodate - for cleavage of diols
LDAlithium diisopropyl amide - strong base (useful for making enolates from carbonyl compounds)


Question Answer
LiAlH4lithium aluminum hydride - strong reducing agent (will reduce esters to alcohols, for instance)
NBSN-bromosuccinimide - brominating reagent.
DCCdicyclohexyl carbodiimide - dehydrating agent for peptide couplings (amine plus carboxylic acid)
KMnO4postassium permanganate - can dihydroxylate alkenes (among other things)
NaBH4sodium borohydride - reducing agent - reduces aldehydes/ketones to alcohols


Question Answer
BH3borane - useful for hydroboration of alkenes (gives anti-Markovnikoff product)
PCCpyridinium chlorochromate - oxidizing agent, will oxidize alcohols to aldehydes/ketones
O3ozone, will cleave double bonds to give aldehydes/ketones/acids (depends on workup)
Hg(OAc)2Mercuric acetate - for oxymercuration of alkenes
R2CuLiOrganocuprate or Gilman reagent - for 1,4-addition on a,B-unsaturated systems


Question Answer
SOCl2Thionyl chloride, for making acid chlorides
Pd/CPalladium on carbon, for hydrogenation of double bonds
K2CrO7Potassium dichromate, oxidizing agent (will convert alcohols to aldehydes)
H2SO4sulfuric acid, strong acid
PBr3Phosphorus tribromide, will convert carboxylic acids to acyl bromides.


Question Answer
HCNhydrogen cyanide, can use to make cyanohydrins
pyrrolidinesecondary amine, for Stork enamine reactions
NCSN-chlorosuccinimide, for chlorinations (similar to NBS)
FeBr3ferric bromide, used for Friedel-Crafts
AlCl3aluminum trichloride, used for Friedel Crafts


Question Answer
Lilithium metal, used to make organolithium from alkyl bromide
Mgmagnesium metal, used to make Grignard from alkyl halide
DMSOpolar aprotic solvent - dimethyl sulfoxide
DMFpolar aprotic solvent - dimethyl formamide
LiAlH(OR)3less reactive derivative of LiAlH4, will reduce esters to aldehydes (only 1 equiv of hydride)


Question Answer
CH2N2diazomethane, will take carboxylic acids to methyl esters
DIBAL-Hdiisobutylaluminum hydride, reducing agent, can take esters to aldehydes.
TsOHp-toluenesulfonic acid, p-TsOH - strong acid. OTs is also good leaving group