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Organic Chemistry: Reactions and Mechanisms

Named reactions, reaction types and what they do.

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  • SN1 reactionReaction
    Two-step substitution through a carbocation; favors tertiary substrates and polar protic solvents
  • SN2 reactionReaction
    One-step substitution with backside attack and inversion; favors methyl and primary substrates
  • E1 reactionReaction
    Two-step elimination through a carbocation
  • E2 reactionReaction
    One-step elimination needing a strong base and anti-periplanar geometry
  • Zaitsev's ruleReaction
    Elimination gives the more substituted alkene as the major product
  • Hofmann productReaction
    The less substituted alkene, favored by bulky bases
  • Carbocation stabilityReaction
    Tertiary > secondary > primary > methyl
  • Leaving groupReaction
    A group that departs with a pair of electrons; good ones are weak bases
  • NucleophileReaction
    An electron-rich species that attacks an electrophile
  • ElectrophileReaction
    An electron-poor species that accepts electrons
  • Polar protic solventReaction
    Solvent with O-H or N-H bonds, like water or ethanol
  • Polar aprotic solventReaction
    Polar solvent without O-H, like acetone or DMSO
  • Electrophilic additionReaction
    Alkene pi bond attacks an electrophile, adding across the double bond
  • HydrohalogenationReaction
    Adding HX across an alkene
  • Hydration of alkenesReaction
    Adding water to form an alcohol
  • HydrogenationReaction
    Adding H2 across a double or triple bond using a metal catalyst
  • Halogenation of alkenesReaction
    Adding X2 across a double bond to give anti addition
  • Hydroboration-oxidationReaction
    Anti-Markovnikov syn addition of water to an alkene
  • Oxymercuration-demercurationReaction
    Markovnikov hydration of alkenes without rearrangements
  • EpoxidationReaction
    Converting an alkene to an epoxide with a peroxyacid
  • OzonolysisReaction
    Cleaving a double bond with ozone to give carbonyls
  • DihydroxylationReaction
    Adding two OH groups across a double bond
  • Free radical halogenationReaction
    Substituting H on an alkane by a halogen through radical steps
  • Radical chain mechanismReaction
    Initiation, propagation, termination
  • Electrophilic aromatic substitutionReaction
    Replacing a hydrogen on an aromatic ring with an electrophile
  • NitrationReaction
    Adding NO2 to an aromatic ring using nitric and sulfuric acid
  • Friedel-Crafts alkylationReaction
    Adding an alkyl group to an aromatic ring using AlCl3
  • Friedel-Crafts acylationReaction
    Adding an acyl group to an aromatic ring
  • Ortho/para directorReaction
    Group that directs incoming electrophiles to positions 2 and 4
  • Meta directorReaction
    Group that directs incoming electrophiles to position 3
  • Activating groupReaction
    Electron-donating group that speeds up aromatic substitution
  • Deactivating groupReaction
    Electron-withdrawing group that slows aromatic substitution
  • Nucleophilic acyl substitutionReaction
    Nucleophile replaces a leaving group on a carbonyl carbon
  • Fischer esterificationReaction
    Acid-catalyzed reaction of a carboxylic acid and alcohol to form an ester
  • SaponificationReaction
    Base hydrolysis of an ester to a carboxylate and alcohol
  • Amide formationReaction
    Reaction of an acid derivative with an amine
  • Grignard reactionReaction
    Organomagnesium reagent adds to carbonyl compounds to form alcohols
  • Organolithium reagentReaction
    Strongly basic carbon nucleophile like Grignards
  • Reduction with NaBH4Reaction
    Mild reduction of aldehydes and ketones to alcohols
  • Reduction with LiAlH4Reaction
    Strong reduction of carbonyls, esters and acids to alcohols
  • PCC oxidationReaction
    Oxidizes primary alcohols to aldehydes
  • Jones oxidationReaction
    Strong oxidation of primary alcohols to carboxylic acids
  • Swern oxidationReaction
    Mild oxidation of alcohols using DMSO
  • Aldol reactionReaction
    An enolate adds to a carbonyl to form a beta-hydroxy carbonyl
  • Aldol condensationReaction
    Aldol addition followed by loss of water
  • Claisen condensationReaction
    Ester enolate attacks another ester to give a beta-keto ester
  • Michael additionReaction
    Nucleophile adds to the beta carbon of an alpha-beta unsaturated carbonyl
  • Wittig reactionReaction
    Converts aldehydes and ketones into alkenes
  • Diels-Alder reactionReaction
    A diene and a dienophile form a six-membered ring
  • CycloadditionReaction
    Concerted reaction forming a ring
  • Williamson ether synthesisReaction
    Alkoxide attacks alkyl halide to form an ether
  • Gabriel synthesisReaction
    Preparing primary amines from alkyl halides using phthalimide
  • Hofmann eliminationReaction
    Converts quaternary ammonium to the less substituted alkene
  • Diazonium saltReaction
    Intermediate from aryl amines used to introduce many groups on rings
  • Sandmeyer reactionReaction
    Replacing a diazonium group with a halide or cyanide using copper salts
  • Cannizzaro reactionReaction
    Aldehydes without alpha hydrogens react to give an alcohol and an acid
  • Baeyer-Villiger oxidationReaction
    Converts ketones into esters using a peracid
  • HydrolysisReaction
    Breaking a bond with water
  • Dehydration of alcoholsReaction
    Acid-catalyzed loss of water to form alkenes
  • TautomerizationReaction
    Interconversion of keto and enol forms
  • Resonance stabilizationReaction
    Delocalization of electrons lowers energy
  • Hammond postulateReaction
    Transition states resemble the nearest-energy species
  • Kinetic vs. thermodynamic controlReaction
    Fastest-formed versus most stable product
  • Inversion of configurationReaction
    Stereochemical result of an SN2 reaction
  • RacemizationReaction
    Formation of equal amounts of both enantiomers
  • Syn additionReaction
    Both groups add to the same face of a double bond
  • Anti additionReaction
    Groups add to opposite faces
  • StereospecificReaction
    Different stereoisomers give different stereoisomeric products
  • RegioselectiveReaction
    One direction of bond making is favored over another
  • Protecting groupReaction
    A temporary group masking a reactive site
  • RetrosynthesisReaction
    Planning a synthesis by working backward from the target
  • Rearrangement (hydride shift)Reaction
    Carbocation moves hydrogen to become more stable
  • PolymerizationReaction
    Joining monomers into long chains
  • Addition polymerReaction
    Polymer formed by adding monomers without losing atoms
  • Condensation polymerReaction
    Polymer formed with loss of a small molecule such as water
  • Beckmann rearrangementReaction
    Oxime converts to an amide under acid
  • Pinacol rearrangementReaction
    Diol converts to a ketone under acid
  • Fries rearrangementReaction
    Aryl ester converts to a hydroxy aryl ketone
  • Clemmensen reductionReaction
    Reduces a ketone or aldehyde to an alkane using zinc and acid
  • Wolff-Kishner reductionReaction
    Reduces a ketone or aldehyde to an alkane under basic conditions
  • Birch reductionReaction
    Reduces aromatic rings to dienes
  • Heck reactionReaction
    Palladium-catalyzed coupling of an alkene with an aryl or vinyl halide
  • Suzuki couplingReaction
    Palladium-catalyzed coupling of organoboron and organohalide
  • Click chemistryReaction
    Fast, reliable reactions that join molecules, like azide-alkyne cycloaddition

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