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Pattern

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Essential Organic Reactions

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Aldol Condensation

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R-CH2CHO+R’-CHOR-CH(OH)-CH(R’)-CHOAldol Product\text{R-CH}_2-\text{CHO} + \text{R'-CHO} \rightarrow \text{R-CH(OH)-CH(R')}\text{-CHO} \rightarrow \text{Aldol Product}

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Schmidt Reaction

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R-C(=O)-R’+HN3+H2SO4R-CONH2+R’SO2OH\text{R-C(=O)-R'} + \text{HN}_3 + \text{H}_2\text{SO}_4 \rightarrow \text{R-CONH}_2 + \text{R'}-\text{SO}_2\text{OH}

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Wacker Oxidation

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Alkene+PdCl2+CuCl2Ketone+Pd+CuCl\text{Alkene} + \text{PdCl}_2 + \text{CuCl}_2 \rightarrow \text{Ketone} + \text{Pd} + \text{CuCl}

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Birch Reduction

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Ar-H+Na/NH31,4-dihydro-Ar\text{Ar-H} + \text{Na}/\text{NH}_3 \rightarrow \text{1,4-dihydro-Ar}

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Baeyer-Villiger Oxidation

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R-C(=O)-R’+PeroxyacidR-C(=O)-O-R’\text{R-C(=O)-R'} + \text{Peroxyacid} \rightarrow \text{R-C(=O)-O-R'}

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Heck Reaction

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Ar-X+Alkene+Pd(0)Ar-Alkene\text{Ar-X} + \text{Alkene} + \text{Pd(0)} \rightarrow \text{Ar-Alkene}

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Finkelstein Reaction

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R-X+NaIacetoneR-I+NaX\text{R-X} + \text{NaI} \xrightarrow{\text{acetone}} \text{R-I} + \text{NaX}

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Sulfonation

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Ar-H+SO3+H2SO4Ar-SO3H+H2O\text{Ar-H} + \text{SO}_3 + \text{H}_2\text{SO}_4 \rightarrow \text{Ar-SO}_3\text{H} + \text{H}_2\text{O}

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Gabriel Synthesis

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Phthalimide+KOH+R-XNHR\text{Phthalimide} + \text{KOH} + \text{R-X} \rightarrow \text{NHR}

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Grignard Reaction

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R-MgX+R’-XR-R’\text{R-MgX} + \text{R'-X} \rightarrow \text{R-R'}

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Reformatsky Reaction

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R-CH2X+R’-C(=O)-R”+ZnR-CH(OH)-CH(R”)-R’\text{R-CH}_2\text{X} + \text{R'-C(=O)-R''} + \text{Zn} \rightarrow \text{R-CH(OH)-CH(R'')-R'}

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Saponification

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R-COOR’+NaOHR-COONa++R’-OH\text{R-COOR'} + \text{NaOH} \rightarrow \text{R-COO}^-\text{Na}^+ + \text{R'-OH}

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Sharpless Dihydroxylation

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Alkene+OsO4+chiral ligandsChiral diol\text{Alkene} + \text{OsO}_4 + \text{chiral ligands} \rightarrow \text{Chiral diol}

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Sandmeyer Reaction

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Ar-N2+X+CuCl/Bcl3Ar-Cl+N2+HX\text{Ar-N}_2^+\text{X}^- + \text{CuCl/Bcl}_3 \rightarrow \text{Ar-Cl} + \text{N}_2 + \text{HX}

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Hydration of Alkenes

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Alkene+H2OacidAlcohol\text{Alkene} + \text{H}_2\text{O} \xrightarrow{\text{acid}} \text{Alcohol}

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Friedel-Crafts Alkylation

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Ar-H+R-ClAlCl3Ar-R+HCl\text{Ar-H} + \text{R-Cl} \xrightarrow{\text{AlCl}_3} \text{Ar-R} + \text{HCl}

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Sharpless Epoxidation

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Allylic alcohol+Ti(OiPr)4+TBHPEpoxide\text{Allylic alcohol} + \text{Ti(OiPr)}_4 + \text{TBHP} \rightarrow \text{Epoxide}

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Suzuki Coupling

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\text{Ar-X} + \text{R-B(OH)_2} \xrightarrow{\text{Pd(0)}} \text{Ar-R}

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Hydroboration-Oxidation

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Alkene+BH3+H2O2,NaOHAlcohol\text{Alkene} + \text{BH}_3 + \text{H}_2\text{O}_2, \text{NaOH} \rightarrow \text{Alcohol}

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Nitration

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Ar-H+HNO3+H2SO4Ar-NO2+H2O\text{Ar-H} + \text{HNO}_3 + \text{H}_2\text{SO}_4 \rightarrow \text{Ar-NO}_2 + \text{H}_2\text{O}

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Wittig Reaction

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R-PPh3+R’-CHOR-CHR’+PPh3O\text{R-PPh}_3 + \text{R'-CHO} \rightarrow \text{R-CHR'} + \text{PPh}_3\text{O}

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OsO4 Oxidation

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Alkene+OsO4+NMOcis-Diol\text{Alkene} + \text{OsO}_4 + \text{NMO} \rightarrow \text{cis-Diol}

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Wolff-Kishner Reduction

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R-C(=O)-R’HNNH2,KOHR-CH2-R’\text{R-C(=O)-R'} \xrightarrow{\text{HNNH}_2, \text{KOH}} \text{R-CH}_2\text{-R'}

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Diels-Alder Reaction

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Diene+DienophileCyclohexene\text{Diene} + \text{Dienophile} \rightarrow \text{Cyclohexene}

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Friedel-Crafts Acylation

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Ar-H+R-CO-ClAlCl3Ar-CO-R+HCl\text{Ar-H} + \text{R-CO-Cl} \xrightarrow{\text{AlCl}_3} \text{Ar-CO-R} + \text{HCl}

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Swern Oxidation

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R-CH2OHDMSO,Oxalyl ChlorideR-CHO\text{R-CH}_2\text{OH} \xrightarrow{\text{DMSO}, \text{Oxalyl Chloride}} \text{R-CHO}

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Hofmann Elimination

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R3N+-CH3XAg2O,H2OR3N+CH2=CH2+AgX+H2O\text{R}_3\text{N}^{+}\text{-CH}_3\text{X}^- \xrightarrow{\text{Ag}_2\text{O}, \text{H}_2\text{O}} \text{R}_3\text{N} + \text{CH}_2=\text{CH}_2 + \text{AgX} + \text{H}_2\text{O}

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Claisen Condensation

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2R-CO-CH2-R’-ROHBaseR-CO-CH2-C(=O)-R’+ROH2 \text{R-CO-CH}_2\text{-R'} \xrightarrow[\text{-ROH}]{\text{Base}} \text{R-CO-CH}_2\text{-C(=O)-R'} + \text{ROH}

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Clemmensen Reduction

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R-C(=O)-R’Zn(Hg),HClR-CH2-R’\text{R-C(=O)-R'} \xrightarrow{\text{Zn(Hg)}, \text{HCl}} \text{R-CH}_2\text{-R'}

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Esterification (Fischer-Speier)

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R-OH+R’-COOHacidR-COOR’+H2O\text{R-OH} + \text{R'-COOH} \xrightarrow{\text{acid}} \text{R-COOR'} + \text{H}_2\text{O}

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