{
 "source": "https://peabody.kids/flashcards/tp-orgchem-reactions",
 "id": "tp-orgchem-reactions",
 "title": "Organic Chemistry: Reactions and Mechanisms",
 "category": "test-prep",
 "subject": "Organic Chemistry",
 "levels": [
  "college"
 ],
 "description": "Named reactions, reaction types and what they do.",
 "tags": [
  "chemistry",
  "organic",
  "reactions"
 ],
 "frontLabel": "Reaction",
 "backLabel": "What happens",
 "cards": [
  [
   "SN1 reaction",
   "Two-step substitution through a carbocation; favors tertiary substrates and polar protic solvents"
  ],
  [
   "SN2 reaction",
   "One-step substitution with backside attack and inversion; favors methyl and primary substrates"
  ],
  [
   "E1 reaction",
   "Two-step elimination through a carbocation"
  ],
  [
   "E2 reaction",
   "One-step elimination needing a strong base and anti-periplanar geometry"
  ],
  [
   "Zaitsev's rule",
   "Elimination gives the more substituted alkene as the major product"
  ],
  [
   "Hofmann product",
   "The less substituted alkene, favored by bulky bases"
  ],
  [
   "Carbocation stability",
   "Tertiary > secondary > primary > methyl"
  ],
  [
   "Leaving group",
   "A group that departs with a pair of electrons; good ones are weak bases"
  ],
  [
   "Nucleophile",
   "An electron-rich species that attacks an electrophile"
  ],
  [
   "Electrophile",
   "An electron-poor species that accepts electrons"
  ],
  [
   "Polar protic solvent",
   "Solvent with O-H or N-H bonds, like water or ethanol"
  ],
  [
   "Polar aprotic solvent",
   "Polar solvent without O-H, like acetone or DMSO"
  ],
  [
   "Electrophilic addition",
   "Alkene pi bond attacks an electrophile, adding across the double bond"
  ],
  [
   "Hydrohalogenation",
   "Adding HX across an alkene"
  ],
  [
   "Hydration of alkenes",
   "Adding water to form an alcohol"
  ],
  [
   "Hydrogenation",
   "Adding H2 across a double or triple bond using a metal catalyst"
  ],
  [
   "Halogenation of alkenes",
   "Adding X2 across a double bond to give anti addition"
  ],
  [
   "Hydroboration-oxidation",
   "Anti-Markovnikov syn addition of water to an alkene"
  ],
  [
   "Oxymercuration-demercuration",
   "Markovnikov hydration of alkenes without rearrangements"
  ],
  [
   "Epoxidation",
   "Converting an alkene to an epoxide with a peroxyacid"
  ],
  [
   "Ozonolysis",
   "Cleaving a double bond with ozone to give carbonyls"
  ],
  [
   "Dihydroxylation",
   "Adding two OH groups across a double bond"
  ],
  [
   "Free radical halogenation",
   "Substituting H on an alkane by a halogen through radical steps"
  ],
  [
   "Radical chain mechanism",
   "Initiation, propagation, termination"
  ],
  [
   "Electrophilic aromatic substitution",
   "Replacing a hydrogen on an aromatic ring with an electrophile"
  ],
  [
   "Nitration",
   "Adding NO2 to an aromatic ring using nitric and sulfuric acid"
  ],
  [
   "Friedel-Crafts alkylation",
   "Adding an alkyl group to an aromatic ring using AlCl3"
  ],
  [
   "Friedel-Crafts acylation",
   "Adding an acyl group to an aromatic ring"
  ],
  [
   "Ortho/para director",
   "Group that directs incoming electrophiles to positions 2 and 4"
  ],
  [
   "Meta director",
   "Group that directs incoming electrophiles to position 3"
  ],
  [
   "Activating group",
   "Electron-donating group that speeds up aromatic substitution"
  ],
  [
   "Deactivating group",
   "Electron-withdrawing group that slows aromatic substitution"
  ],
  [
   "Nucleophilic acyl substitution",
   "Nucleophile replaces a leaving group on a carbonyl carbon"
  ],
  [
   "Fischer esterification",
   "Acid-catalyzed reaction of a carboxylic acid and alcohol to form an ester"
  ],
  [
   "Saponification",
   "Base hydrolysis of an ester to a carboxylate and alcohol"
  ],
  [
   "Amide formation",
   "Reaction of an acid derivative with an amine"
  ],
  [
   "Grignard reaction",
   "Organomagnesium reagent adds to carbonyl compounds to form alcohols"
  ],
  [
   "Organolithium reagent",
   "Strongly basic carbon nucleophile like Grignards"
  ],
  [
   "Reduction with NaBH4",
   "Mild reduction of aldehydes and ketones to alcohols"
  ],
  [
   "Reduction with LiAlH4",
   "Strong reduction of carbonyls, esters and acids to alcohols"
  ],
  [
   "PCC oxidation",
   "Oxidizes primary alcohols to aldehydes"
  ],
  [
   "Jones oxidation",
   "Strong oxidation of primary alcohols to carboxylic acids"
  ],
  [
   "Swern oxidation",
   "Mild oxidation of alcohols using DMSO"
  ],
  [
   "Aldol reaction",
   "An enolate adds to a carbonyl to form a beta-hydroxy carbonyl"
  ],
  [
   "Aldol condensation",
   "Aldol addition followed by loss of water"
  ],
  [
   "Claisen condensation",
   "Ester enolate attacks another ester to give a beta-keto ester"
  ],
  [
   "Michael addition",
   "Nucleophile adds to the beta carbon of an alpha-beta unsaturated carbonyl"
  ],
  [
   "Wittig reaction",
   "Converts aldehydes and ketones into alkenes"
  ],
  [
   "Diels-Alder reaction",
   "A diene and a dienophile form a six-membered ring"
  ],
  [
   "Cycloaddition",
   "Concerted reaction forming a ring"
  ],
  [
   "Williamson ether synthesis",
   "Alkoxide attacks alkyl halide to form an ether"
  ],
  [
   "Gabriel synthesis",
   "Preparing primary amines from alkyl halides using phthalimide"
  ],
  [
   "Hofmann elimination",
   "Converts quaternary ammonium to the less substituted alkene"
  ],
  [
   "Diazonium salt",
   "Intermediate from aryl amines used to introduce many groups on rings"
  ],
  [
   "Sandmeyer reaction",
   "Replacing a diazonium group with a halide or cyanide using copper salts"
  ],
  [
   "Cannizzaro reaction",
   "Aldehydes without alpha hydrogens react to give an alcohol and an acid"
  ],
  [
   "Baeyer-Villiger oxidation",
   "Converts ketones into esters using a peracid"
  ],
  [
   "Hydrolysis",
   "Breaking a bond with water"
  ],
  [
   "Dehydration of alcohols",
   "Acid-catalyzed loss of water to form alkenes"
  ],
  [
   "Tautomerization",
   "Interconversion of keto and enol forms"
  ],
  [
   "Resonance stabilization",
   "Delocalization of electrons lowers energy"
  ],
  [
   "Hammond postulate",
   "Transition states resemble the nearest-energy species"
  ],
  [
   "Kinetic vs. thermodynamic control",
   "Fastest-formed versus most stable product"
  ],
  [
   "Inversion of configuration",
   "Stereochemical result of an SN2 reaction"
  ],
  [
   "Racemization",
   "Formation of equal amounts of both enantiomers"
  ],
  [
   "Syn addition",
   "Both groups add to the same face of a double bond"
  ],
  [
   "Anti addition",
   "Groups add to opposite faces"
  ],
  [
   "Stereospecific",
   "Different stereoisomers give different stereoisomeric products"
  ],
  [
   "Regioselective",
   "One direction of bond making is favored over another"
  ],
  [
   "Protecting group",
   "A temporary group masking a reactive site"
  ],
  [
   "Retrosynthesis",
   "Planning a synthesis by working backward from the target"
  ],
  [
   "Rearrangement (hydride shift)",
   "Carbocation moves hydrogen to become more stable"
  ],
  [
   "Polymerization",
   "Joining monomers into long chains"
  ],
  [
   "Addition polymer",
   "Polymer formed by adding monomers without losing atoms"
  ],
  [
   "Condensation polymer",
   "Polymer formed with loss of a small molecule such as water"
  ],
  [
   "Beckmann rearrangement",
   "Oxime converts to an amide under acid"
  ],
  [
   "Pinacol rearrangement",
   "Diol converts to a ketone under acid"
  ],
  [
   "Fries rearrangement",
   "Aryl ester converts to a hydroxy aryl ketone"
  ],
  [
   "Clemmensen reduction",
   "Reduces a ketone or aldehyde to an alkane using zinc and acid"
  ],
  [
   "Wolff-Kishner reduction",
   "Reduces a ketone or aldehyde to an alkane under basic conditions"
  ],
  [
   "Birch reduction",
   "Reduces aromatic rings to dienes"
  ],
  [
   "Heck reaction",
   "Palladium-catalyzed coupling of an alkene with an aryl or vinyl halide"
  ],
  [
   "Suzuki coupling",
   "Palladium-catalyzed coupling of organoboron and organohalide"
  ],
  [
   "Click chemistry",
   "Fast, reliable reactions that join molecules, like azide-alkyne cycloaddition"
  ]
 ]
}