Organic Chemistry Reagent Guide Organic Chemistry Reagent Guide

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Acetone Polar aprotic solvent; see "Solvents" page Ether Diethyl ether Solvent (see "Solvents" page)
AgNO3 Silver nitrate SN1 reactions FeBr3 Iron (III) Bromide Catalyst for additions to aromatic rings
Ag2O Silver oxide Used in the Tollens reaction
Grignard Reagents RMgX Adds carbon groups to ketones, esters, aldehydes...
AIBN Initiator for free radical reactions
AlBr3 Aluminum bromide Catalyst for additions to aromatic rings HBr Hydrobromic acid Strong acid, adds to alkenes and alkynes
AlCl3 Aluminum chloride Catalyst for additions to aromatic rings
HCl Hydrochloric acid Strong acid, adds to alkenes and alkynes
BH3 Borane Hydroboration
H2CrO4 Chromic acid Strong oxidant for alcohols
Br2 Bromine Adds to alkenes, aromatic rings
Hg(OAc)2 Mercuric Acetate For oxymercuration of alkenes and alkynes
BsCl Benzenesulfonyl Converts alcohols to good leaving groups
chloride HI Hydroiodic acid Strong acid, adds to alkenes and alkynes
O
S Cl HONO Nitrous acid Forms diazonium salts from aromatic amines
O HIO4 Hydroiodic acid Oxidant, forms aldehydes/ketones from vicinal diols
CCl4 Carbon tetrachloride Nonpolar solvent; see "Solvents" page
H2O2 Hydrogen peroxide Oxidant, for hydroboration and ozonolysis
Cl2 Chlorine Adds to alkenes, aromatic rings
I2 Iodine Adds to alkenes and alkynes
CN Cyanide Good nucleophile
KMnO4 Potassium permanganate Oxidant for alkenes, alcohols, aldehydes, alkanes
CrO3 Chromium Trioxide Oxidant for alcohols and aldehydes Potassium Dichromate
K2Cr2O7 See H2CrO4
CuBr Copper Bromide Adds Br to aromatic rings; forms organocuprates KCN Potassium cyanide See CN

KOtBu Potassium t-butoxide Bulky base

CuCN Copper Cyanide Adds CN to aromatic rings
LDA Lithium diisopropyl amide Strong bulky base
CuCl Copper Chloride Adds Cl to aromatic rings; forms organocuprates
CuI Copper Iodide Forms organocuprates N
DCC Dicyclohexane Reagent for forming amides from carobyxlic acids Li
carbodiimide and amines LiAlH4 Lithium aluminum hydride Strong reducing agent for carbonyl compounds
Lindlar's catalyst Reducing agent for alkynes to give cis-alkenes
LiAl(Ot-Bu)3 Bulky reducing agent for acid chlorides to give aldehydes
N C N mCPBA m-chloroperbenzoic acid Oxidant, gives epoxides from alkenes

DMF N,N'-dimethylformamide Polar aprotic solvent (see "Solvents" page) Cl

O
DMS Dimethyl sulfide For reductive workup in ozonolysis
DMSO Dimethyl sulfoxide Polar aprotic solvent; see "Solvents" page O OH
Diazomethane CH2N2 Forms methyl esters, used in the Wolff Rearrangement MsCl Methanesulfonyl chloride Converts alcohols into good leaving groups
O
DIBAL Diisobutyl aluminum Bulky reducing agent for esters, nitriles
hydride H3C S Cl
O

Al
H
Organic Chemistry Reagent Guide Organic Chemistry Reagent Guide

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N3 Azide Good nucleophile PCC Pyridinium chlorochromate Oxidizes alcohols to aldehydes/ketones

Na Sodium Reducing agent for alkynes, aromatic groups O

Cl Cr O
NaBH4 Sodium Borohydride Reduces aldehydes/ketones to alcohols N
O
H
Ph3P Triphenyl phosphine Used in the Wittig reaction
NaCN Sodium cyanide See CN
Na2Cr2O7 Sodium Dichromate See H2CrO4 Pyr Pyridine Weak base
NaH Sodium Hydride Strong base, poor nucleophile

NaIO4 Sodium periodate Cleaves 1,2-diols to carbonyls N

Raney Nickel Reducing agent, replaces sulfur with H

NaNH2 Sodium amide Strong base
RO-OR "Peroxides" Free radical initiator
NaOtBu Sodium t-butoxide See KOtBu
SO3 Sulfur Trioxide For installation of SO3H on an aromatic ring

NBS N-Bromo succinimide Source of bromine, used for allylic bromination SOBr2 Thionyl bromide Converts alcohols/acids to alkyl / acyl bromides

SOCl2 Thionyl chloride Converts alcohols/acids to alkyl/acyl chlorides

O N O Sn Tin For reduction of nitro groups to amines
Br
THF Tetrahydrofuran Solvent (see "Solvents" page)
NCS N-chloro succinimide Source of chlorine, used in alkene addition reactions
NH2OH Hydroxylamine Formation of oximes
TsCl Tosyl chloride Converts alcohols to tosylates (good leaving group)
NIS N-Iodo succinimide Sources of iodine, used in alkenes addition reactions
O
NH3 Ammonia Base, occasional solvent S Cl
NH2NH2 Hydrazine Good nucleophile, used in the Wolff-Kishner reaction O
TsOH Tosic acid Strong acid
Ni2B Nickel Boride Reduces alkynes to cis-alkenes
O
OsO4 Osmium Tetraoxide Converts alkenes to cis-diols (glycols) S OH
O
O3 Ozone Cleaves double and triple bonds to carbonyl compounds
Zn Zinc Reducing agent, for ozonolysis and nitro groups
Organocuprates R2CuLi Adds carbon groups to double bonds, alkyl halides
Zn(Hg) Zinc amalgam For Clemmensen reduction, ketones to alkanes
Organolithium reagents RLi Adds carbon groups to carbonyl compounds
Zn(Cu) Zinc-copper couple For cyclopropanation reactions with CH2I2

Pb(OAc)4 Lead tetra-acetate Cleaves 1,2-diols to carbonyl compounds

PBr3 Phosphorus Tribromide Converts alcohols/ acids to alkyl / acyl bromides

PCl3 Phosphorus Trichloride Converts alcohols/ acids to alkyl / acyl chlorides

P2O5 Phosphorus Pentoxide Converts acids to anhydrides, amides to nitriles

Pt Platinum For reduction of double / triple bonds with H2

Pd/C Palladium on carbon For reduction of double / triple bonds with H2