Octet / Collection
Reactions
Reaction references and mechanisms
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All Reactions
Reaction references and mechanisms
SN2 with Hydroxide
SN2 with Hydroxide (SN2 Substitution.) Converts CCBr to CCO using NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion).
SN2 with Cyanide
SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.
SN1 Solvolysis
SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...
SN2 with Tosylate Leaving Group
SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.
SN2 with Azide
SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.
E2 Elimination
E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using 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..
E1 Elimination
E1 Elimination (E1 Elimination.) Converts CC(C)(C)Br to CC(C)=C using Weak base or heat. Conditions: Polar protic solvent, heat in Water or alcohol. Stereochemistry: No stereospecificity (unlike E2).
Alcohol Dehydration
Alcohol Dehydration (E1 Elimination.) Converts CC(C)(C)O to CC(C)=C using H₂SO₄, H₃PO₄. Conditions: Concentrated acid, heat.
Hofmann Elimination
Hofmann Elimination (E2 Elimination.) Converts CC(C)C[N+](C)(C)C to C=CC(C)C using Ag₂O/H₂O then heat, NaOH, heat. Conditions: Heat.
Hydrohalogenation (HX Addition)
Hydrohalogenation (HX Addition) (Electrophilic Addition Addition.) Converts CC=C to CC(C)Br using HBr (or HCl, HI).
Hydroboration-Oxidation
Hydroboration-Oxidation (Syn Addition Addition.) Converts CC=C to CCCO using 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).
Oxymercuration-Demercuration
Oxymercuration-Demercuration (Electrophilic Addition Addition.) Converts CC=C to CC(C)O using Hg(OAc)₂/H₂O, then NaBH₄. Stereochemistry: Anti addition.
Halogenation of Alkene
Halogenation of Alkene (Electrophilic Addition Addition.) Converts CC=CC to CC(Br)C(Br)C using Br₂ (or Cl₂). Stereochemistry: Anti addition (trans-dihalide from cis-alkene).
Halohydrin Formation
Halohydrin Formation (Addition.) Converts CC=CC to CC(O)C(Br)C using Br₂/H₂O (or Cl₂/H₂O). Stereochemistry: Anti addition.
Epoxidation (with mCPBA)
Epoxidation (with mCPBA) (Addition.) Converts CC=CC to CC1OC1C using mCPBA, MMPP, peracetic acid. Stereochemistry: Syn addition (stereochemistry of alkene preserved).
Syn Dihydroxylation (OsO₄)
Syn Dihydroxylation (OsO₄) (Addition.) Converts CC=CC to CC(O)C(O)C using OsO₄, cat. OsO₄ with NMO. Stereochemistry: Syn addition (both OHs on same face).
Anti Dihydroxylation (Epoxide Opening)
Anti Dihydroxylation (Epoxide Opening) (Addition.) Converts CC1OC1C to CC(O)C(O)C using H₃O⁺/H₂O, or NaOH/H₂O. Stereochemistry: Anti addition (OHs on opposite faces).
Catalytic Hydrogenation
Catalytic Hydrogenation (Reduction Addition.) Converts CC=CC to CCCC using H₂, Pd/C or Pt or Ni. Conditions: H₂ gas, metal catalyst. Stereochemistry: Syn addition.
Lindlar Reduction (Alkyne → cis-Alkene)
Lindlar Reduction (Alkyne → cis-Alkene) (Reduction Addition.) Converts CC#CC to C/C=C\C using H₂, Lindlar catalyst (Pd/CaCO₃/Pb). Stereochemistry: Syn addition → cis-alkene.
Dissolving Metal Reduction (Alkyne → trans-Alkene)
Dissolving Metal Reduction (Alkyne → trans-Alkene) (Reduction Addition.) Converts CC#CC to C/C=C/C using Na or Li, NH₃ (liquid). Conditions: -33°C (liquid ammonia). Stereochemistry: Anti addition → trans-alkene.
PCC Oxidation (1° Alcohol → Aldehyde)
PCC Oxidation (1° Alcohol → Aldehyde) (Oxidation.) Converts CCO to CC=O using PCC (pyridinium chlorochromate).
Jones Oxidation (Alcohol → Carboxylic Acid)
Jones Oxidation (Alcohol → Carboxylic Acid) (Oxidation.) Converts CCO to CC(=O)O using CrO₃/H₂SO₄/acetone, Jones reagent.
Swern Oxidation
Swern Oxidation (Oxidation.) Converts CCO to CC=O using (COCl)₂ (oxalyl chloride), DMSO, Et₃N. Conditions: -78°C.
KMnO₄ Oxidative Cleavage
KMnO₄ Oxidative Cleavage (Oxidation.) Converts CC=CC to CC(=O)O.CC(=O)O using KMnO₄ (hot, concentrated). Conditions: Heat, aqueous.
Ozonolysis
Ozonolysis (Oxidation.) Converts CC=CC to CC=O.CC=O using O₃, then Zn/H₂O or DMS. Conditions: -78°C.
NaBH₄ Reduction (Aldehyde/Ketone → Alcohol)
NaBH₄ Reduction (Aldehyde/Ketone → Alcohol) (Reduction.) Converts CC=O to CCO using NaBH₄.
LiAlH₄ Reduction
LiAlH₄ Reduction (Reduction.) Converts CC(=O)OC to CCO.CO using LiAlH₄.
DIBAL Reduction (Ester → Aldehyde)
DIBAL Reduction (Ester → Aldehyde) (Reduction.) Converts CC(=O)OC to CC=O using DIBAL-H (diisobutylaluminum hydride). Conditions: -78°C, 1 equivalent.
Clemmensen Reduction (C=O → CH₂)
Clemmensen Reduction (C=O → CH₂) (Reduction.) Converts c1ccc(C(=O)C)cc1 to c1ccc(CC)cc1 using Zn(Hg), HCl (conc.). Conditions: Heat.
Wolff-Kishner Reduction
Wolff-Kishner Reduction (Reduction.) Converts c1ccc(C(=O)C)cc1 to c1ccc(CC)cc1 using NH₂NH₂ (hydrazine), KOH, heat. Conditions: High temperature, ethylene glycol.
Nitration of Benzene
Nitration of Benzene (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1[N+](=O)[O-] using HNO₃, H₂SO₄. Conditions: Heat.
Halogenation of Benzene
Halogenation of Benzene (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1Br using Br₂, FeBr₃ (or AlBr₃).
Friedel-Crafts Alkylation
Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1C(C)C using (CH₃)₂CHCl, AlCl₃.
Friedel-Crafts Acylation
Friedel-Crafts Acylation (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1C(=O)C using CH₃COCl, AlCl₃.
Sulfonation of Benzene
Sulfonation of Benzene (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1S(=O)(=O)O using SO₃, H₂SO₄ (fuming).
Grignard Addition to Carbonyl
Grignard Addition to Carbonyl (Carbonyl.) Converts CC=O to CC(C)O using CH₃MgBr, then H₃O⁺. Conditions: Anhydrous ether, then acid workup.
Aldol Addition
Aldol Addition (Carbonyl.) Converts CC=O to CC(O)CC=O using NaOH (dilute), LDA. Conditions: Low temperature for addition (warm for condensation).
Aldol Condensation
Aldol Condensation (Carbonyl.) Converts CC=O to CC=CC=O using NaOH, heat.
Wittig Reaction
Wittig Reaction (Carbonyl.) Converts CC=O to CC=C using Ph₃P=CH₂ (ylide).
Claisen Condensation
Claisen Condensation (Carbonyl.) Converts CC(=O)OCC to CC(=O)CC(=O)OCC using NaOEt, EtOH.
Fischer Esterification
Fischer Esterification (Carbonyl.) Converts CC(=O)O to CC(=O)OC using MeOH, H₂SO₄ (cat.). Conditions: Reflux, remove water.
Acyl Chloride Formation
Acyl Chloride Formation (Carbonyl.) Converts CC(=O)O to CC(=O)Cl using SOCl₂, or PCl₃, or PCl₅.
Amide Formation from Acyl Chloride
Amide Formation from Acyl Chloride (Carbonyl.) Converts CC(=O)Cl to CC(=O)NC using CH₃NH₂, excess amine or with base.
Diels-Alder Reaction
Diels-Alder Reaction (Pericyclic.) Converts C=CC=C.C=C to C1CC=CCC1 using Heat (or Lewis acid catalyst). Conditions: Heat or pressure. Stereochemistry: Syn addition on both components. Endo product kinetically favored..
Michael Addition
Michael Addition (Conjugate Addition Carbonyl.) Converts CC(=O)C=C to CC(=O)CCC#N using Nucleophile (enolate, CN⁻, amine, thiol).
Alcohol to Alkyl Bromide (PBr₃)
Alcohol to Alkyl Bromide (PBr₃) (Substitution.) Converts CCO to CCBr using PBr₃. Stereochemistry: Inversion (SN2 mechanism).
Alcohol to Alkyl Chloride (SOCl₂)
Alcohol to Alkyl Chloride (SOCl₂) (Substitution.) Converts CCO to CCCl using SOCl₂, pyridine (optional).
Baeyer-Villiger Oxidation
Baeyer-Villiger Oxidation (Oxidation.) Converts CC(=O)c1ccccc1 to CC(=O)Oc1ccccc1 using mCPBA, CF₃CO₃H, peracetic acid.
Beckmann Rearrangement
Beckmann Rearrangement (Rearrangement.) Converts CC(c1ccccc1)=NO to CC(=O)Nc1ccccc1 using H₂SO₄, PCl₅, SOCl₂. Conditions: Acidic conditions, heat.
Pinacol Rearrangement
Pinacol Rearrangement (Rearrangement.) Converts CC(O)(C)C(O)(C)C to CC(=O)C(C)(C)C using H₂SO₄, H₃PO₄. Conditions: Acidic conditions, heat.
Curtius Rearrangement
Curtius Rearrangement (Rearrangement.) Converts CC(=O)N=[N+]=[N-] to CN=C=O using Heat or photolysis. Conditions: Heat or UV light.
Hofmann Rearrangement
Hofmann Rearrangement (Rearrangement.) Converts CC(=O)N to CN using Br₂, NaOH. Conditions: Aqueous base.
Cannizzaro Reaction
Cannizzaro Reaction (Oxidation.) Converts c1ccccc1C=O to c1ccccc1CO.c1ccccc1C(=O)[O-] using NaOH (conc.), KOH. Conditions: Strong base, no α-hydrogens.
Gabriel Synthesis
Gabriel Synthesis (Substitution.) Converts O=C1c2ccccc2C(=O)N1 to CCN using R-X (1° alkyl halide), then N₂H₄ or NaOH/heat.
Reductive Amination
Reductive Amination (Reduction.) Converts CC=O to CCNC using R-NH₂, then NaBH₃CN or NaBH(OAc)₃.
Strecker Synthesis
Strecker Synthesis (Addition.) Converts CC=O to CC(N)C(=O)O using NH₃, HCN, then H₃O⁺.
Henry Reaction (Nitroaldol)
Henry Reaction (Nitroaldol) (Addition.) Converts CC=O to CC(O)C[N+](=O)[O-] using R-NO₂, base (NaOH, Et₃N).
Mannich Reaction
Mannich Reaction (Addition.) Converts CC(=O)C to CC(=O)CCN(C)C using HCHO, R₂NH (or NH₃), acid catalyst.
Robinson Annulation
Robinson Annulation (Carbonyl.) Converts CC(=O)CC(=O)C to CC1=CC(=O)CCC1 using MVK (methyl vinyl ketone), base.
Simmons-Smith Cyclopropanation
Simmons-Smith Cyclopropanation (Addition.) Converts CC=CC to CC1CC1C using CH₂I₂, Zn-Cu couple (or Et₂Zn). Stereochemistry: Syn addition - cyclopropane stereochemistry reflects alkene geometry.
Birch Reduction
Birch Reduction (Reduction.) Converts c1ccccc1 to C1=CCC=CC1 using Na or Li, NH₃(l), ROH. Conditions: -33°C (liquid ammonia).
Suzuki-Miyaura Coupling
Suzuki-Miyaura Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1c2ccccc2 using PhB(OH)₂ (aryl boronic acid), Pd(PPh₃)₄, base (Na₂CO₃).
Heck Reaction
Heck Reaction (Coupling.) Converts c1ccccc1Br to c1ccccc1/C=C/C using Alkene, Pd(OAc)₂, base (Et₃N), phosphine ligand.
Sonogashira Coupling
Sonogashira Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1C#CC using Terminal alkyne, Pd catalyst, CuI (co-catalyst), amine base.
Negishi Coupling
Negishi Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1CC using R-ZnX (organozinc), Pd catalyst.
Stille Coupling
Stille Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1C=C using R-SnBu₃ (organostannane), Pd catalyst.
Mitsunobu Reaction
Mitsunobu Reaction (Substitution.) Converts CC(C)O to CC(C)N3 using DEAD or DIAD, PPh₃, Nucleophile (pKa < 15). Stereochemistry: Inversion of configuration (like SN2).
Appel Reaction
Appel Reaction (Substitution.) Converts CCO to CCBr using CBr₄, PPh₃.
Dess-Martin Oxidation
Dess-Martin Oxidation (Oxidation.) Converts CCO to CC=O using DMP (Dess-Martin periodinane).
Sharpless Asymmetric Epoxidation
Sharpless Asymmetric Epoxidation (Addition.) Converts C/C=C/CO to CC1OC1CO using TBHP (t-BuOOH), Ti(OiPr)₄, Tartrate ester (D or L). Stereochemistry: Enantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack.
Williamson Ether Synthesis
Williamson Ether Synthesis (Substitution.) Converts C[O-] to COC using R-X (alkyl halide), alkoxide.
Acid-Catalyzed Ester Hydrolysis
Acid-Catalyzed Ester Hydrolysis (Carbonyl.) Converts CC(=O)OCC to CC(=O)O.CCO using H₂O, H₂SO₄ or HCl. Conditions: Aqueous acid, reflux.
Saponification (Base-Catalyzed Ester Hydrolysis)
Saponification (Base-Catalyzed Ester Hydrolysis) (Carbonyl.) Converts CC(=O)OCC to CC(=O)[O-].CCO using NaOH, KOH. Conditions: Aqueous base, reflux.
Enamine Formation
Enamine Formation (Carbonyl.) Converts CC(=O)CC to CC(=CN(C)C)C using R₂NH (2° amine), acid catalyst. Conditions: Remove water (Dean-Stark).
Acetal Formation
Acetal Formation (Carbonyl.) Converts CC=O to CC(OC)OC using ROH (excess), acid catalyst. Conditions: Remove water.
Hell-Volhard-Zelinsky Reaction
Hell-Volhard-Zelinsky Reaction (Substitution.) Converts CCC(=O)O to CC(Br)C(=O)O using Br₂, PBr₃ or P.
Cope Rearrangement
Cope Rearrangement (Pericyclic.) Converts C=CCC=CC to CC=CCC=C using Heat. Conditions: Thermal (150-200°C). Stereochemistry: Chair-like transition state preferred.
Claisen Rearrangement
Claisen Rearrangement (Pericyclic.) Converts C=CCOC=C to C=CCC(=O)C using Heat. Conditions: Thermal (150-200°C).
Olefin Metathesis
Olefin Metathesis (Coupling.) Converts C=CC to CC=CC using Grubbs catalyst (Ru-based).
Anti-Markovnikov HBr Addition (Radical)
Anti-Markovnikov HBr Addition (Radical) (Addition.) Converts CC=C to CCCBr using HBr, ROOR (peroxide). Conditions: Peroxide initiator (light or heat).
Reformatsky Reaction
Reformatsky Reaction (Addition.) Converts BrCC(=O)OCC to CC(O)CC(=O)OCC using α-Bromo ester, Zn, aldehyde or ketone.
Malonic Ester Synthesis
Malonic Ester Synthesis (Substitution.) Converts CCOC(=O)CC(=O)OCC to CCC(=O)O using NaOEt, R-X, then H₃O⁺/heat.
Acetoacetic Ester Synthesis
Acetoacetic Ester Synthesis (Substitution.) Converts CCOC(=O)CC(=O)C to CCC(=O)C using NaOEt, R-X, then H₃O⁺/heat.
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