Miscellaneous Reagents

pizayize's version from 2017-06-17 00:05


Question Answer
OsO4osmium tetroxide - Alkene to 2 syn alcohols
Pb(OAc)4lead tetraacetate - for cleavage of diols. Cuts between the 2 alcohols, creating c=o bond
mCPBAmeta chloro perbenzoic acid - alkene to epoxide
NaIO4sodium periodate - for cleavage of diols. Cuts between the 2 alcohols, creating c=o bond. (same process as Pb(OAc)4
LDAlithium diisopropyl amide - Attaches something 1 carbon away from ketone.


Question Answer
LiAlH4lithium aluminum hydride - strong reducing agent (ketone to alcohol. Carboxylic acid and derivatives to aldehydes)
NBSN-bromosuccinimide - brominating reagent. Adds bromine 1 carbon away from c=c bond
KMnO4postassium permanganate - benzylic H to COOH
NaBH4sodium borohydride - reducing agent - reduces aldehydes/ketones to alcohols


Question Answer
BH3borane - alkene to alcohol (keto-group if more stable). Gives anti-Markovnikoff product
PCCpyridinium chlorochromate - oxidizing agent, will oxidize primary alcohols to aldehydes and secondary/tertiary alcohols to ketones
O3ozone, will cleave double bonds to give aldehydes/ketones/acids (depends on workup)
Hg(OAc)2Mercuric acetate - alkene to markovnikov alcohol


Question Answer
SOCl2Thionyl chloride, for making acid chlorides
K2CrO7Potassium dichromate, primary alcohol and aldehydes to COOH and secondary alcohol to ketones.
H2SO4sulfuric acid, strong acid that eliminates OH groups. Similar to H3PO4
PBr3Phosphorus tribromide, Similar to SOCl2. SN2 addition of bromine to alcohol. COOH goes to COOBr


Question Answer
HCNhydrogen cyanide, turns c=o to an oh and adds the CN group.
NCSN-chlorosuccinimide, Similar to NBS. Adds Cl 1 carbon away from c=c bond
FeBr3ferric bromide, adds Br to aromatic ring
AlCl3aluminum trichloride, adds Cl to aromatic ring


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


Question Answer
CH2N2diazomethane, will take carboxylic acids to methyl esters
TsOHp-toluenesulfonic acid, p-TsOH - strong acid. OTs is also good leaving group