Organic Reagents

Ag₂O (Silver Oxide)

an oxidizing agent used in Tollens' reagent to convert aldehydes into carboxylic acids

AlBr₃ (Aluminum Bromide)

a strong Lewis acid catalyst used to chlorinate or alkylate aromatic rings via electrophilic aromatic substitution

AlCl₃ (Aluminum Chloride)

a common Lewis acid catalyst used in Friedel-Crafts alkylation and acylation reactions

Br₂ (Bromine)

a liquid halogen electrophile that adds across alkenes to form vicinal dibromides

Cl₂ (Chlorine)

a gaseous halogen electrophile used for the chlorination of alkanes and alkenes

CN (Cyanide Ion and Nitrile Group)

a strong carbon-centered nucleophile used to extend a carbon chain by one atom via substitution reactions

CrO₃ (Chromium Trioxide)

a strong chromium-based oxidizing agent that converts primary alcohols into carboxylic acids and secondary alcohols into ketones

CuBr (Copper (I) Bromide)

a transition metal salt used in the Sandmeyer reaction to replace aryl diazonium groups with bromine

CuCl (Copper (I) Chloride)

a transition metal salt used in the Sandmeyer reaction to replace aryl diazonium groups with chlorine

CuI (Copper (I) Iodide)

a copper source used to synthesize organocuprate reagents and catalyze cross-coupling reactions

DCC (N,N′-Dicyclohexylcarbodiimide)

a dehydrating coupling agent used to synthesize amides and esters from carboxylic acids

DMS (Dimethyl Sulfide)

a mild reducing agent used during the reductive workup of alkene ozonolysis reactions

CH₂N₂ (Diazomethane)

a highly reactive, explosive methylating agent used to convert carboxylic acids into methyl esters

D (Deuterium)

a heavy stable isotope of hydrogen used to trace reaction mechanisms and study kinetic isotope effects

DIBAL (Diisobutylaluminum Hydride)

a bulky, selective reducing hydride agent that reduces esters and nitriles to aldehydes at low temperatures

DMP (Dess-Martin Periodinane)

a mild, hypervalent iodine oxidizing agent that converts primary alcohols to aldehydes without over-oxidation

DMSO (Dimethyl Sulfoxide)

a polar aprotic solvent frequently used in nucleophilic substitutions and Swern oxidations

EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide)

a water-soluble carbodiimide coupling agent used to form amide bonds from carboxylic acids and amines

Fe (Iron)

a transition metal reducing agent used with acid to reduce nitroarenes to primary anilines

FeBr₃ (Iron (III) Bromide)

a Lewis acid catalyst required to facilitate the electrophilic bromination of benzene rings

FeCl₃ (Iron (III) Chloride)

a Lewis acid catalyst used to facilitate electrophilic aromatic chlorinations and alkylations

RMgX (Grignard Reagents)

highly basic, strongly nucleophilic organometallic compounds used to form new carbon-carbon single bonds

H₂ (Hydrogen)

a diatomic gas used alongside transition metal catalysts to reduce alkenes and alkynes to alkanes

H⁺ and H₃O⁺ (Hydronium Ion)

an aqueous acid catalyst used for proton transfer steps, hydrolyses, and alkene hydrations

HBr (Hydrobromic Acid)

a strong mineral acid that adds across alkenes to form alkyl bromides with Markovnikov regioselectivity

HCl (Hydrochloric Acid)

a strong mineral acid used as a proton source and a source of nucleophilic chloride ions

HI (Hydroiodic Acid)

a strong mineral acid commonly used to cleave ethers into alkyl iodides and alcohols

H₂CrO₄ (Chromic Acid)

a strong, aggressive oxidizing agent that converts primary alcohols directly into carboxylic acids

Hg(OAc)₂ (Mercuric Acetate)

an electrophilic mercury reagent used in oxymercuration-demercuration to hydrate alkenes without carbocation rearrangements

HgSO₄ (Mercuric Sulfate)

a Lewis acid catalyst used to accelerate the hydration of terminal alkynes into methyl ketones

HIO₄ (Periodic Acid)

an oxidizing agent used to oxidatively cleave vicinal diols into two separate carbonyl compounds

HONO (Nitrous Acid)

an unstable weak acid generated in situ to convert primary aromatic amines into highly reactive diazonium salts

HNO₃ (Nitric Acid)

a strong acid and strong oxidizing agent mixed with sulfuric acid to generate nitronium ions for aromatic nitration

H₂O₂ (Hydrogen Peroxide)

an oxidizing agent used to replace carbon-boron bonds with carbon-hydroxyl bonds during hydroboration-oxidation workups

H₃PO₄ (Phosphoric Acid)

a non-nucleophilic mineral acid catalyst favored for the dehydration of alcohols into alkenes

H₂SO₄ (Sulfuric Acid)

a strong, dehydrating mineral acid catalyst used in Fischer esterifications and nitration mixtures

I₂ (Iodine)

a halogen electrophile used for the iodination of aromatic rings and the iodoform test for methyl ketones

KMeans₄ (Potassium Permanganate)

a powerful oxidizing agent that yields syn-1,2-diols when cold and cleaves carbon-carbon double bonds when hot

tBuOK (Potassium tert-Butoxide)

a strong, sterically hindered, non-nucleophilic base used to favor Hofmann elimination products

LDA (Lithium Diisopropylamide)

a strong, sterically hindered, non-nucleophilic base used to cleanly generate kinetic enolates at low temperatures

Li (Lithium)

a reactive alkali metal used to prepare organolithium reagents or to drive Birch reductions in liquid ammonia

Lindlar’s Catalyst

a deactivated palladium catalyst used to selectively reduce alkynes to cis-alkenes without over-reduction

LiAlH₄ (Lithium Aluminum Hydride)

a powerful, unselective reducing hydride agent that reduces carbonyls, esters, and carboxylic acids to alcohols

LiAlH(Ot-Bu)₃ (Lithium Tri-tert-Butoxy Aluminum Hydride)

a hindered, mild hydride reducing agent designed to selectively reduce acyl chlorides to aldehydes

MCPBA (m-Chloroperoxybenzoic Acid)

a peroxyacid oxidizing agent used to convert alkenes to epoxides and ketones to esters

Mg (Magnesium)

a metal that undergoes oxidative insertion into alkyl halides to form nucleophilic Grignard reagents

MsCl (Methanesulfonyl Chloride)

a reagent used to convert poorly leaving hydroxyl groups into excellent mesylate leaving groups

NaN₃ (Sodium Azide)

a salt source of the highly nucleophilic azide ion used in substitution reactions

Na (Sodium)

a reactive alkali metal used in dissolving metal reductions to convert internal alkynes into trans-alkenes

NaBH₄ (Sodium Borohydride)

a mild, selective reducing hydride agent that reduces aldehydes and ketones but ignores esters and acids

NaCNBH₃ (Sodium Cyanoborohydride)

an acid-stable, selective reducing agent optimized for reducing imines to amines during reductive aminations

NaBH(OAc)₃ (Sodium Triacetoxyborohydride)

a mild, selective reducing agent used specifically for the reductive amination of carbonyl compounds

NaH (Sodium Hydride)

a powerful, non-nucleophilic base used primarily for deprotonating alcohols to generate alkoxide ions

NaIO₄ (Sodium Periodate)

an oxidizing agent used for the oxidative cleavage of vicinal diols and the oxidation of sulfides

NaNH₂ (Sodium Amide)

an exceptionally strong base used to deprotonate terminal alkynes or generate benzyne intermediates

NaOH (Sodium Hydroxide)

a versatile strong base and nucleophile used in ester saponifications and aldol condensations

NaOEt (Sodium Ethoxide)

a strong base and nucleophile commonly used to generate enolates or promote E2 eliminations with ethyl esters

NBS (N-Bromosuccinimide)

a regulated source of bromine radicals used for allylic and benzylic bromination reactions

NCS (N-Chlorosuccinimide)

a regulated source of chlorine radicals used for allylic and benzylic chlorination reactions

NIS (N-Iodosuccinimide)

a source of electrophilic iodine used in iodination reactions and halohydrin formations

NH₂OH (Hydroxylamine)

a nitrogen-centered nucleophile that condenses with aldehydes and ketones to yield crystalline oximes

NH₃ (Ammonia)

a volatile weak base and nucleophile used to synthesize primary amides or act as a solvent in Birch reductions

NH₂NH₂ (Hydrazine)

a powerful nucleophile used in Wolff-Kishner reductions to reduce carbonyl groups to methylene units

Ni₂B (Nickel Boride)

a selective heterogeneous catalyst used for the syn-hydrogenation of alkynes to cis-alkenes

O₃ (Ozone)

a reactive triatomic gas used to oxidatively cleave alkenes and alkynes down the unsaturated bond

R₂CuLi ((Gilman) Organocuprates)

mild organometallic nucleophiles that undergo conjugate 1,4-additions with alpha,beta-unsaturated carbonyls and substitute alkyl halides

RLi (Organolithium Reagents)

highly reactive, strongly basic organometallic carbon nucleophiles that readily add to carbonyl compounds

OsO₄ (Osmium Tetroxide)

a highly toxic, selective oxidizing catalyst used to convert alkenes into syn-1,2-diols

Pb(OAc)₄ (Lead Tetraacetate)

an oxidizing agent used to oxidatively cleave vicinal diols, functioning similarly to periodic acid

PBr₃ (Phosphorus Tribromide)

a halogenating reagent used to convert primary and secondary alcohols into alkyl bromides with inversion of configuration

PCl₃ (Phosphorus Trichloride)

a halogenating reagent used to convert primary and secondary alcohols into alkyl chlorides

PCl₅ (Phosphorus Pentachloride)

a strong chlorinating agent used to convert carboxylic acids into acyl chlorides and carbonyls into gem-dichlorides

Pd/C (Palladium on Carbon)

a heterogeneous metal catalyst used with hydrogen gas to reduce pi bonds

Pt (Platinum)

a noble transition metal catalyst used to facilitate the catalytic hydrogenation of unsaturated organic molecules

PCC (Pyridinium Chlorochromate)

a mild chromium-based oxidizing agent that converts primary alcohols to aldehydes without over-oxidizing to carboxylic acids

POCl₃ (Phosphorus Oxychloride)

a dehydrating agent used to convert alcohols into alkenes via an E2 elimination mechanism

Ph₃P (Triphenylphosphine)

a phosphorus nucleophile used to prepare phosphonium ylides for the Wittig alkene synthesis reaction

PPI (Potassium Phthalimide)

a protected nucleophilic nitrogen source used in the Gabriel synthesis to cleanly prepare primary amines