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Reactions
Reaction references and mechanisms
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All Reactions
Reaction references and mechanisms
SN2 with Hydroxide
SN2 with Hydroxide (SN2 Substitution). Starts from Bromoethane with NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion). Mechanism in 3 steps.
SN2 with Cyanide
SN2 with Cyanide (SN2 Substitution). Starts from Iodoethane with NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration. Mechanism in 3 steps.
SN1 Solvolysis
SN1 Solvolysis (SN1 Substitution). Starts from Tertiary bromide with H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)...
SN2 with Tosylate Leaving Group
SN2 with Tosylate Leaving Group (SN2 Substitution). Starts from Ethyl tosylate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.
SN2 with Azide
SN2 with Azide (SN2 Substitution). Starts from Alkyl bromide substrate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.
E2 Elimination
E2 Elimination (E2 Elimination). Starts from 2-Bromobutane with KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed.. Mechanism in 3 steps.
E1 Elimination
E1 Elimination (E1 Elimination). Starts from Tertiary bromide with Weak base or heat. Conditions: Polar protic solvent, heat in Water or alcohol. Stereochemistry: No stereospecificity (unlike E2). Mechanism in 3 steps.
Alcohol Dehydration
Alcohol Dehydration (E1 Elimination). Starts from Tertiary alcohol with H₂SO₄, H₃PO₄. Conditions: Concentrated acid, heat. Mechanism in 4 steps.
Hofmann Elimination
Hofmann Elimination (E2 Elimination). Reagents: Ag₂O/H₂O then heat, NaOH, heat. Conditions: Heat. Mechanism in 2 steps.
Hydrohalogenation (HX Addition)
Hydrohalogenation (HX Addition) (Electrophilic Addition Addition). Starts from Propene with HBr (or HCl, HI). Mechanism in 4 steps.
Hydroboration-Oxidation
Hydroboration-Oxidation (Syn Addition Addition). Starts from Propene with BH₃·THF, then H₂O₂/NaOH. Conditions: THF solvent, 0°C for BH₃, then oxidation. Stereochemistry: Syn addition (H and OH end up on same face). Mechanism in 3 steps.
Oxymercuration-Demercuration
Oxymercuration-Demercuration (Electrophilic Addition Addition). Starts from Propene with Hg(OAc)₂/H₂O, then NaBH₄. Stereochemistry: Anti addition. Mechanism in 3 steps.
Halogenation of Alkene
Halogenation of Alkene (Electrophilic Addition Addition). Starts from 2-Butene with Br₂ (or Cl₂). Stereochemistry: Anti addition (trans-dihalide from cis-alkene). Mechanism in 4 steps.
Halohydrin Formation
Halohydrin Formation (Addition). Starts from 2-Butene with Br₂/H₂O (or Cl₂/H₂O). Stereochemistry: Anti addition. Mechanism in 3 steps.
Epoxidation (with mCPBA)
Epoxidation (with mCPBA) (Addition). Starts from 2-Butene with mCPBA, MMPP, peracetic acid. Stereochemistry: Syn addition (stereochemistry of alkene preserved). Mechanism in 2 steps.
Syn Dihydroxylation (OsO₄)
Syn Dihydroxylation (OsO₄) (Addition). Starts from 2-Butene with OsO₄, cat. OsO₄ with NMO. Stereochemistry: Syn addition (both OHs on same face). Mechanism in 3 steps.
Anti Dihydroxylation (Epoxide Opening)
Anti Dihydroxylation (Epoxide Opening) (Addition). Starts from Epoxide with H₃O⁺/H₂O, or NaOH/H₂O. Stereochemistry: Anti addition (OHs on opposite faces). Mechanism in 2 steps.
Catalytic Hydrogenation
Catalytic Hydrogenation (Reduction Addition). Starts from 2-Butene with H₂, Pd/C or Pt or Ni. Conditions: H₂ gas, metal catalyst. Stereochemistry: Syn addition. Mechanism in 2 steps.
Lindlar Reduction (Alkyne → cis-Alkene)
Lindlar Reduction (Alkyne → cis-Alkene) (Reduction Addition). Starts from 2-Butyne (internal alkyne) with H₂, Lindlar catalyst (Pd/CaCO₃/Pb). Stereochemistry: Syn addition → cis-alkene. Mechanism in 2 steps.
Dissolving Metal Reduction (Alkyne → trans-Alkene)
Dissolving Metal Reduction (Alkyne → trans-Alkene) (Reduction Addition). Starts from 2-Butyne with Na or Li, NH₃ (liquid). Conditions: -33°C (liquid ammonia). Stereochemistry: Anti addition → trans-alkene. Mechanism in 2 steps.
PCC Oxidation (1° Alcohol → Aldehyde)
PCC Oxidation (1° Alcohol → Aldehyde) (Oxidation). Starts from Primary alcohol (ethanol) with PCC (pyridinium chlorochromate). Mechanism in 2 steps.
Jones Oxidation (Alcohol → Carboxylic Acid)
Jones Oxidation (Alcohol → Carboxylic Acid) (Oxidation). Starts from Ethanol with CrO₃/H₂SO₄/acetone, Jones reagent. Mechanism in 3 steps.
Swern Oxidation
Swern Oxidation (Oxidation). Starts from Primary alcohol with (COCl)₂ (oxalyl chloride), DMSO, Et₃N. Conditions: -78°C. Mechanism in 2 steps.
KMnO₄ Oxidative Cleavage
KMnO₄ Oxidative Cleavage (Oxidation). Starts from 2-Butene with KMnO₄ (hot, concentrated). Conditions: Heat, aqueous. Mechanism in 2 steps.
Ozonolysis
Ozonolysis (Oxidation). Starts from 2-Butene with O₃, then Zn/H₂O or DMS. Conditions: -78°C. Mechanism in 2 steps.
NaBH₄ Reduction (Aldehyde/Ketone → Alcohol)
NaBH₄ Reduction (Aldehyde/Ketone → Alcohol) (Reduction). Starts from Acetaldehyde with NaBH₄. Mechanism in 2 steps.
LiAlH₄ Reduction
LiAlH₄ Reduction (Reduction). Starts from Methyl acetate (ester) with LiAlH₄. Mechanism in 2 steps.
DIBAL Reduction (Ester → Aldehyde)
DIBAL Reduction (Ester → Aldehyde) (Reduction). Starts from Methyl acetate with DIBAL-H (diisobutylaluminum hydride). Conditions: -78°C, 1 equivalent. Mechanism in 2 steps.
Clemmensen Reduction (C=O → CH₂)
Clemmensen Reduction (C=O → CH₂) (Reduction). Starts from Acetophenone with Zn(Hg), HCl (conc.). Conditions: Heat. Mechanism in 2 steps.
Wolff-Kishner Reduction
Wolff-Kishner Reduction (Reduction). Starts from Acetophenone with NH₂NH₂ (hydrazine), KOH, heat. Conditions: High temperature, ethylene glycol. Mechanism in 3 steps.
Nitration of Benzene
Nitration of Benzene (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with HNO₃, H₂SO₄. Conditions: Heat. Mechanism in 3 steps.
Halogenation of Benzene
Halogenation of Benzene (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with Br₂, FeBr₃ (or AlBr₃). Mechanism in 3 steps.
Friedel-Crafts Alkylation
Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with (CH₃)₂CHCl, AlCl₃. Mechanism in 3 steps.
Friedel-Crafts Acylation
Friedel-Crafts Acylation (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with CH₃COCl, AlCl₃. Mechanism in 3 steps.
Sulfonation of Benzene
Sulfonation of Benzene (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with SO₃, H₂SO₄ (fuming). Mechanism in 2 steps.
Grignard Addition to Carbonyl
Grignard Addition to Carbonyl (Carbonyl). Starts from Acetaldehyde with CH₃MgBr, then H₃O⁺. Conditions: Anhydrous ether, then acid workup. Mechanism in 3 steps.
Aldol Addition
Aldol Addition (Carbonyl). Starts from Acetaldehyde with NaOH (dilute), LDA. Conditions: Low temperature for addition (warm for condensation). Mechanism in 3 steps.
Aldol Condensation
Aldol Condensation (Carbonyl). Starts from Acetaldehyde with NaOH, heat. Mechanism in 3 steps.
Wittig Reaction
Wittig Reaction (Carbonyl). Starts from Acetaldehyde with Ph₃P=CH₂ (ylide). Mechanism in 3 steps.
Claisen Condensation
Claisen Condensation (Carbonyl). Starts from Ethyl acetate with NaOEt, EtOH. Mechanism in 3 steps.
Fischer Esterification
Fischer Esterification (Carbonyl). Starts from Acetic acid with MeOH, H₂SO₄ (cat.). Conditions: Reflux, remove water. Mechanism in 3 steps.
Acyl Chloride Formation
Acyl Chloride Formation (Carbonyl). Starts from Acetic acid with SOCl₂, or PCl₃, or PCl₅. Mechanism in 2 steps.
Amide Formation from Acyl Chloride
Amide Formation from Acyl Chloride (Carbonyl). Starts from Acetyl chloride with CH₃NH₂, excess amine or with base. Mechanism in 2 steps.
Diels-Alder Reaction
Diels-Alder Reaction (Pericyclic). Starts from Diene (1,3-butadiene) in s-cis conformation with Heat (or Lewis acid catalyst). Conditions: Heat or pressure. Stereochemistry: Syn addition on both components. Endo product kinetically favored.. Mechanism in 3 st...
Michael Addition
Michael Addition (Conjugate Addition Carbonyl). Starts from α,β-unsaturated ketone (MVK) with Nucleophile (enolate, CN⁻, amine, thiol). Mechanism in 2 steps.
Alcohol to Alkyl Bromide (PBr₃)
Alcohol to Alkyl Bromide (PBr₃) (Substitution). Starts from Ethanol with PBr₃. Stereochemistry: Inversion (SN2 mechanism). Mechanism in 3 steps.
Alcohol to Alkyl Chloride (SOCl₂)
Alcohol to Alkyl Chloride (SOCl₂) (Substitution). Starts from Ethanol with SOCl₂, pyridine (optional). Mechanism in 2 steps.
Baeyer-Villiger Oxidation
Baeyer-Villiger Oxidation (Oxidation). Starts from Acetophenone with mCPBA, CF₃CO₃H, peracetic acid. Mechanism in 3 steps.
Beckmann Rearrangement
Beckmann Rearrangement (Rearrangement). Starts from Oxime starting material (from ketone + NH₂OH) with H₂SO₄, PCl₅, SOCl₂. Conditions: Acidic conditions, heat. Mechanism in 3 steps.
Pinacol Rearrangement
Pinacol Rearrangement (Rearrangement). Starts from Pinacol with H₂SO₄, H₃PO₄. Conditions: Acidic conditions, heat. Mechanism in 3 steps.
Curtius Rearrangement
Curtius Rearrangement (Rearrangement). Starts from Acyl azide (from acid chloride + NaN₃) with Heat or photolysis. Conditions: Heat or UV light. Mechanism in 2 steps.
Hofmann Rearrangement
Hofmann Rearrangement (Rearrangement). Starts from Amide starting material with Br₂, NaOH. Conditions: Aqueous base. Mechanism in 3 steps.
Cannizzaro Reaction
Cannizzaro Reaction (Oxidation). Starts from Benzaldehyde with NaOH (conc.), KOH. Conditions: Strong base, no α-hydrogens. Mechanism in 3 steps.
Gabriel Synthesis
Gabriel Synthesis (Substitution). Starts from Potassium phthalimide (phthalimide + KOH) with R-X (1° alkyl halide), then N₂H₄ or NaOH/heat. Mechanism in 3 steps.
Reductive Amination
Reductive Amination (Reduction). Starts from Aldehyde or ketone with R-NH₂, then NaBH₃CN or NaBH(OAc)₃. Mechanism in 3 steps.
Strecker Synthesis
Strecker Synthesis (Addition). Starts from Aldehyde with NH₃, HCN, then H₃O⁺. Mechanism in 4 steps.
Henry Reaction (Nitroaldol)
Henry Reaction (Nitroaldol) (Addition). Starts from Aldehyde with R-NO₂, base (NaOH, Et₃N). Mechanism in 3 steps.
Mannich Reaction
Mannich Reaction (Addition). Starts from Enolizable ketone with HCHO, R₂NH (or NH₃), acid catalyst. Mechanism in 3 steps.
Robinson Annulation
Robinson Annulation (Carbonyl). Starts from β-Diketone or other enolizable ketone with MVK (methyl vinyl ketone), base. Mechanism in 3 steps.
Simmons-Smith Cyclopropanation
Simmons-Smith Cyclopropanation (Addition). Starts from 2-Butene (alkene substrate) with CH₂I₂, Zn-Cu couple (or Et₂Zn). Stereochemistry: Syn addition - cyclopropane stereochemistry reflects alkene geometry. Mechanism in 2 steps.
Birch Reduction
Birch Reduction (Reduction). Starts from Benzene with Na or Li, NH₃(l), ROH. Conditions: -33°C (liquid ammonia). Mechanism in 3 steps.
Suzuki-Miyaura Coupling
Suzuki-Miyaura Coupling (Coupling). Starts from Aryl halide (bromobenzene) with PhB(OH)₂ (aryl boronic acid), Pd(PPh₃)₄, base (Na₂CO₃). Mechanism in 3 steps.
Heck Reaction
Heck Reaction (Coupling). Starts from Aryl halide with Alkene, Pd(OAc)₂, base (Et₃N), phosphine ligand. Mechanism in 3 steps.
Sonogashira Coupling
Sonogashira Coupling (Coupling). Starts from Aryl halide with Terminal alkyne, Pd catalyst, CuI (co-catalyst), amine base. Mechanism in 3 steps.
Negishi Coupling
Negishi Coupling (Coupling). Starts from Aryl halide with R-ZnX (organozinc), Pd catalyst. Mechanism in 3 steps.
Stille Coupling
Stille Coupling (Coupling). Starts from Aryl halide with R-SnBu₃ (organostannane), Pd catalyst. Mechanism in 3 steps.
Mitsunobu Reaction
Mitsunobu Reaction (Substitution). Starts from Secondary alcohol with DEAD or DIAD, PPh₃, Nucleophile (pKa < 15). Stereochemistry: Inversion of configuration (like SN2). Mechanism in 3 steps.
Appel Reaction
Appel Reaction (Substitution). Starts from Alcohol with CBr₄, PPh₃. Mechanism in 3 steps.
Dess-Martin Oxidation
Dess-Martin Oxidation (Oxidation). Starts from Primary alcohol with DMP (Dess-Martin periodinane). Mechanism in 2 steps.
Sharpless Asymmetric Epoxidation
Sharpless Asymmetric Epoxidation (Addition). Starts from Allylic alcohol (must have OH) with TBHP (t-BuOOH), Ti(OiPr)₄, Tartrate ester (D or L). Stereochemistry: Enantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack. Mechanism in 2 steps.
Williamson Ether Synthesis
Williamson Ether Synthesis (Substitution). Starts from Methoxide anion (from NaH + MeOH) with R-X (alkyl halide), alkoxide. Mechanism in 3 steps.
Acid-Catalyzed Ester Hydrolysis
Acid-Catalyzed Ester Hydrolysis (Carbonyl). Starts from Ethyl acetate (ester) with H₂O, H₂SO₄ or HCl. Conditions: Aqueous acid, reflux. Mechanism in 3 steps.
Saponification (Base-Catalyzed Ester Hydrolysis)
Saponification (Base-Catalyzed Ester Hydrolysis) (Carbonyl). Starts from Ethyl acetate with NaOH, KOH. Conditions: Aqueous base, reflux. Mechanism in 3 steps.
Enamine Formation
Enamine Formation (Carbonyl). Starts from 2-Butanone (ketone) with R₂NH (2° amine), acid catalyst. Conditions: Remove water (Dean-Stark). Mechanism in 2 steps.
Acetal Formation
Acetal Formation (Carbonyl). Starts from Aldehyde with ROH (excess), acid catalyst. Conditions: Remove water. Mechanism in 3 steps.
Hell-Volhard-Zelinsky Reaction
Hell-Volhard-Zelinsky Reaction (Substitution). Starts from Carboxylic acid with Br₂, PBr₃ or P. Mechanism in 3 steps.
Cope Rearrangement
Cope Rearrangement (Pericyclic). Starts from 1,5-Hexadiene with Heat. Conditions: Thermal (150-200°C). Stereochemistry: Chair-like transition state preferred. Mechanism in 2 steps.
Claisen Rearrangement
Claisen Rearrangement (Pericyclic). Starts from Allyl vinyl ether with Heat. Conditions: Thermal (150-200°C). Mechanism in 2 steps.
Olefin Metathesis
Olefin Metathesis (Coupling). Starts from Propene (two equivalents) with Grubbs catalyst (Ru-based). Mechanism in 2 steps.
Anti-Markovnikov HBr Addition (Radical)
Anti-Markovnikov HBr Addition (Radical) (Addition). Starts from Propene with HBr, ROOR (peroxide). Conditions: Peroxide initiator (light or heat). Mechanism in 3 steps.
Reformatsky Reaction
Reformatsky Reaction (Addition). Starts from Ethyl bromoacetate with α-Bromo ester, Zn, aldehyde or ketone. Mechanism in 3 steps.
Malonic Ester Synthesis
Malonic Ester Synthesis (Substitution). Starts from Diethyl malonate with NaOEt, R-X, then H₃O⁺/heat. Mechanism in 3 steps.
Acetoacetic Ester Synthesis
Acetoacetic Ester Synthesis (Substitution). Starts from Ethyl acetoacetate with NaOEt, R-X, then H₃O⁺/heat. Mechanism in 3 steps.
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