Organic Chemistry Reagent Guide Organic Chemistry Reagent GuideQuick Index Quick Index 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 R–MgX 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 used in alkenes addition reactions O NH3 Ammonia Base. for ozonolysis and nitro groups Organocuprates R2CuLi Adds carbon groups to double bonds.Organic Chemistry Reagent Guide Organic Chemistry Reagent Guide Quick Index Quick Index N3 Azide Good nucleophile PCC Pyridinium chlorochromate Oxidizes alcohols to aldehydes/ketones Na Sodium Reducing agent for alkynes.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. ketones to alkanes Organolithium reagents R–Li Adds carbon groups to carbonyl compounds Zn(Cu) Zinc-copper couple For cyclopropanation reactions with CH2I2 Pb(OAc)4 Lead tetra-acetate Cleaves 1. 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.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. 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. 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. 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 . 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. poor nucleophile NaIO4 Sodium periodate Cleaves 1. alkyl halides Zn(Hg) Zinc amalgam For Clemmensen reduction. occasional solvent S Cl NH2NH2 Hydrazine Good nucleophile.