Organic Chemistry Reagent Guide

Organic Chemistry Reagent Guide

Quick Index
Acetone AgNO3 Ag2O AIBN AlBr3 AlCl3 BH3 Br2 BsCl Aluminum bromide Aluminum chloride Borane Bromine Benzenesulfonyl chloride O S Cl O Carbon tetrachloride Chlorine Cyanide Chromium Trioxide Copper Bromide Copper Cyanide Copper Chloride Copper Iodide Dicyclohexane carbodiimide Silver nitrate Silver oxide Polar aprotic solvent; see "Solvents" page SN1 reactions Used in the Tollens reaction Initiator for free radical reactions Catalyst for additions to aromatic rings Catalyst for additions to aromatic rings Hydroboration Adds to alkenes, aromatic rings Converts alcohols to good leaving groups Ether FeBr3 Diethyl ether Iron (III) Bromide RMgX

Quick Index
Solvent (see "Solvents" page) Catalyst for additions to aromatic rings Adds carbon groups to ketones, esters, aldehydes... Strong acid, adds to alkenes and alkynes Strong acid, adds to alkenes and alkynes Strong oxidant for alcohols For oxymercuration of alkenes and alkynes Strong acid, adds to alkenes and alkynes Forms diazonium salts from aromatic amines Oxidant, forms aldehydes/ketones from vicinal diols Oxidant, for hydroboration and ozonolysis Adds to alkenes and alkynes Oxidant for alkenes, alcohols, aldehydes, alkanes See H2CrO4 See CN Bulky base Strong bulky base

Grignard Reagents HBr HCl H2CrO4

Hydrobromic acid Hydrochloric acid Chromic acid

Hg(OAc)2 Mercuric Acetate HI HONO HIO4 Hydroiodic acid Nitrous acid Hydroiodic acid Hydrogen peroxide Iodine Potassium permanganate Potassium Dichromate Potassium cyanide Potassium t-butoxide Lithium diisopropyl amide

CCl4 Cl2 CN CrO3 CuBr CuCN CuCl CuI DCC

Nonpolar solvent; see "Solvents" page Adds to alkenes, aromatic rings Good nucleophile Oxidant for alcohols and aldehydes Adds Br to aromatic rings; forms organocuprates Adds CN to aromatic rings Adds Cl to aromatic rings; forms organocuprates Forms organocuprates Reagent for forming amides from carobyxlic acids and amines

H2O2 I2 KMnO4 K2Cr2O7 KCN KOtBu LDA

N Li LiAlH4 Lithium aluminum hydride Lindlar's catalyst LiAl(Ot-Bu)3 mCPBA m-chloroperbenzoic acid Cl O O OH MsCl Methanesulfonyl chloride O H3C S Cl O

Strong reducing agent for carbonyl compounds Reducing agent for alkynes to give cis-alkenes Bulky reducing agent for acid chlorides to give aldehydes Oxidant, gives epoxides from alkenes

N C N DMF DMS DMSO N,N'-dimethylformamide Dimethyl sulfide Dimethyl sulfoxide Polar aprotic solvent (see "Solvents" page) For reductive workup in ozonolysis Polar aprotic solvent; see "Solvents" page Forms methyl esters, used in the Wolff Rearrangement Bulky reducing agent for esters, nitriles

Diazomethane CH2N2 DIBAL Diisobutyl aluminum hydride

Converts alcohols into good leaving groups

Al H

Organic Chemistry Reagent Guide

Organic Chemistry Reagent Guide

Quick Index
N3 Na NaBH4 NaCN Na2Cr2O7 NaH NaIO4 NaNH2 NaOtBu NBS Azide Sodium Sodium Borohydride Sodium cyanide Sodium Dichromate Sodium Hydride Sodium periodate Sodium amide Sodium t-butoxide N-Bromo succinimide O N Br N-chloro succinimide Hydroxylamine N-Iodo succinimide Ammonia Hydrazine Nickel Boride Osmium Tetraoxide Ozone O Good nucleophile Reducing agent for alkynes, aromatic groups Reduces aldehydes/ketones to alcohols See CN See H2CrO4 Strong base, poor nucleophile Cleaves 1,2-diols to carbonyls Strong base See KOtBu Source of bromine, used for allylic bromination N Raney Nickel RO-OR SO3 SOBr2 SOCl2 Sn Source of chlorine, used in alkene addition reactions Formation of oximes Sources of iodine, used in alkenes addition reactions Base, occasional solvent Good nucleophile, used in the Wolff-Kishner reaction Reduces alkynes to cis-alkenes Converts alkenes to cis-diols (glycols) Cleaves double and triple bonds to carbonyl compounds Zn Organocuprates R2CuLi Organolithium reagents Pb(OAc)4 PBr3 PCl3 P2O5 Pt Pd/C RLi Adds carbon groups to double bonds, alkyl halides Zn(Hg) Adds carbon groups to carbonyl compounds Cleaves 1,2-diols to carbonyl compounds Converts alcohols/ acids to alkyl / acyl bromides Converts alcohols/ acids to alkyl / acyl chlorides Converts acids to anhydrides, amides to nitriles For reduction of double / triple bonds with H2 For reduction of double / triple bonds with H2 Zn(Cu) Zinc amalgam Zinc-copper couple Zinc TsOH Tosic acid O S OH O THF "Peroxides" Sulfur Trioxide Thionyl bromide Thionyl chloride Tin Tetrahydrofuran Ph3P Pyr PCC Pyridinium chlorochromate O Cl Cr O O Triphenyl phosphine Pyridine

Quick Index
Oxidizes alcohols to aldehydes/ketones

N H Used in the Wittig reaction Weak base

Reducing agent, replaces sulfur with H Free radical initiator For installation of SO3H on an aromatic ring Converts alcohols/acids to alkyl / acyl bromides Converts alcohols/acids to alkyl/acyl chlorides For reduction of nitro groups to amines Solvent (see "Solvents" page)

NCS NH2OH NIS NH3 NH2NH2 Ni2B OsO4 O3

TsCl

Tosyl chloride O S Cl O

Converts alcohols to tosylates (good leaving group)

Strong acid

Reducing agent, for ozonolysis and nitro groups For Clemmensen reduction, ketones to alkanes For cyclopropanation reactions with CH2I2

Lead tetra-acetate Phosphorus Tribromide Phosphorus Trichloride Phosphorus Pentoxide Platinum Palladium on carbon