Organic Chemistry Reagents
AgBF4
Used in SN1 reactions
AgNO3
Used in the Tollens reaction
AlBr3
Catalyst for additions to aromatic rings
AlCl3
Catalyst for additions to aromatic rings
BH3
Borane
Br2
Adds to alkenes, aromatic rings
BsCl
Converts alcohols to good leaving groups
CCl4
Nonpolar solvent; see “Solvents” page
Cl2
Adds to alkenes, aromatic rings
CN
Good nucleophile
CrO3
Oxidant for alcohols and aldehydes
CuBr
Adds Br to aromatic rings; forms organocuprates
DCC
Reagent for forming amides from carboyxlic acids and amines
DMS
For reductive workup in ozonolysis
FeBr3
Catalyst for additions to aromatic rings
Gringard Reagents R-MgX
Adds carbon groups to ketones, esters, aldehydes…
HBr
Strong acid, adds to alkenes and alkynes
HCl
Strong acid, adds to alkenes and alkynes
H2CrO4
Strong oxidant for alcohols
Hg(OAc)2
For oxymercuration of alkenes and alkynes
HI
Strong acid forms aldehydes/ketones from vicinal diols
HIO4
Oxidant, forms aldehydes/ketones from vicinal diols
HNO3
Strong acid, adds NO2 to aromatics
H2O2
Oxidant, for hydroboration and ozonolysis
H2SO4
Strong acid, useful for elimination reactions
I2
Adds to alkenes and alkynes
KMnO4
Oxidant for alkenes, alcohols, aldehydes, alkanes
KOtBu
Bulky base, used for elimination reactions
LDA
Strong bulky base, for formation of enolates
Li
Reducing metal, for formation of organolithiums
Lindlar’s catalyst
Reducing agent for alkynes to give cis-alkenes
LiAlH4
Strong reducing agent for carbonyl compounds
Mg
Reducing metal, for formation of Grignard reagents
NaN3
Good nucleophile
Na
Reducing agent for alkynes, aromatic groups
NaBH4
Reduces aldehydes/ketones to alcohols
NaH
Strong base, poor nucleophile
NaNH2
Strong Base
NBS
Source of bromine, used for allylic bromination
NH3
Base, occasional solvent
NH2NH2
Good nucleophile, used in the Wolff-Kishner reaction
Ni-B
educes alkynes to cis-alkenes
O3
Cleaves double and triple bonds to carbonyl compounds
Organolithium reagents R-Li
Adds carbon groups to carbonyl compounds
OsO4
Converts alkenes to cis 1,2-diols (glycols)
Pt
For reduction of double / triple bonds with H2
Pd
For reduction of double / triple bonds with H2
PCC
Oxidizes alcohols to aldehydes/ketones
Ph3P
Used in the Wittig reaction
Pyr
Weak base
SO3
For installation of SO3H on an aromatic ring
TsCl
Converts alcohols to tosylates (good leaving group)
TsOH
Strong acid
Zn
Reducing agent, for ozonolysis and nitro groups
Zn(Hg)
For Clemmensen reduction, ketones to alkanes