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The Reaction Guide gives individual descriptions, examples, and mechanisms of more than 185 of the most common reactions encountered in undergraduate organic chemistry. Only members can access all of the full pages. Reactions highlighted in red are open-access.
Alkanes
Alkenes
Alkynes
Substitution (SN2)
Substitution (SN1)
Elimination Reactions
Alcohols and Thiols
Organometallics
Epoxides
Dienes
Aromatics (Arenes)
Aldehydes and Ketones
Carboxylic Acids
Esters
Acyl Halides
α,β-unsaturated alkenes
Amides
Nitriles
Miscellaneous
Alkanes
Free radical chlorination [hν, Cl2]
Free radical bromination [hν, Br2]
Allylic bromination [NBS]
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Alkenes
Addition of HCl
Addition of HBr
Addition of HI
Addition of H3O(+)
Chlorination [Cl2]
Bromination [Br2]
Iodination [I2]
Chlorohydrin formation [Cl2/H2O]
Bromohydrin formation [Br2/H2O]
Ether Formation [H+/ROH]
Oxymercuration [Hg(OAc)2/H2O]
Oxymercuration [Hg(OAc)2/ROH]
Hydroboration
Epoxidation [RCO3H]
Dihydroxylation [OsO4]
Dihydroxylation [KMnO4]
Cyclopropanation
Dichlorocyclopropanation
Ozonolysis (Reductive workup)
Ozonolysis (Oxidative workup)
Oxidative Cleavage [KMnO4]
Hydrogenation
Rearrangements (H shift)
Rearrangements (Alkyl shift)
Free Radical Addition of HBr
Sharpless Epoxidation
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Alkynes
Deprotonation (acetylide formation)
SN2 with alkyl halides
Partial reduction (Lindlar)
Partial reduction [Na/NH3]
Hydroboration
Oxymercuration
Addition of HCl, HBr, or HI (once)
Addition of HCl, HBr, or HI (twice)
Hydrogenation
Ozonolysis
Oxidative cleavage [KMnO4]
Alkyne formation via elimination
Halogenation [Cl2, Br2, I2]
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Substitution Reactions (SN2) [nucleophile in brackets]
Alcohol formation [HO(–)]
Alcohol formation [H2O]
Nitrile formation [CN(-)]
Thiol formation [HS(–)]
Ether formation [RO(–)] Williamson
Thioether formation [RS( –)]
Azides [N3(–)]
Ester formation [RCO2(–)]
Acetylide addition [RC≡C(–)]
Alkanes [Gilman reagents]
Alcohol formation [thru ether cleavage]
Ammonium salt formation [RNH2]
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Substitution Reactions (SN1) [nucleophile in brackets]
Alcohol formation [H2O]
Ether formation [ROH]
Alcohol formation [ether cleavage]
Alkyl chloride formation [HCl]
Alkyl bromide formation [HBr]
Alkyl iodide formation [HI]
SN1 w/ rearrangement [alkyl shift]
SN1 w/rearrangement [hydride shift]
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Elimination Reactions
E2: Alkenes from alkyl halides
Alkenes from alcohols [strong acid]
Alkenes from alcohols [POCl3]
E1: Alkenes from alkyl halides
E1 with rearrangement [alkyl shift]
Hoffmann Elimination
Alkyne formation via elimination
E1 with rearrangement [hydride shift]
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Reactions of Organometallics
Grignard formation [alkyl halides]
Grignard formation [alkenyl halides]
Reaction of Grignards with acid [H+]
Addition of Grignards to aldehydes
Addition of Grignards to ketones
Addition of Grignards to esters
Reaction of Grignards with CO2
Addition of Grignards to nitriles
Formation of organolithium reagents
Formation of Gilman reagents
SN2 with Gilman reagents
Addition of Gilman reagents to enones
Addition of Gilman to acyl halides
Heck Reaction
Suzuki Reaction
Stille Reaction
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Reactions of Epoxides
Epoxide opening [basic conditions]
Epoxide opening [acidic conditions]
Epoxide opening [diol formation]
Epoxide formation [from halohydrins]
Epoxide formation [from alkenes]
Sharpless Epoxidation of alkenes
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Reactions of Alcohols and Thiols
Deprotonation [alkoxide formation]
Protonation [onium ion formation]
Conversion to ethers [Williamson reaction]
Conversion to tosylates/mesylates
Conversion to alkyl chlorides [SOCl2]
Conversion to alkyl bromides [PBr3]
Oxidation to aldehydes [PCC]
Oxidation to ketones [PCC + others]
Oxidation to carboxylic acids [H2CrO4 + others]
Protection as silyl ethers
Thiol formation [SN2]
Thiol oxidation to disulfides
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Reactions of Dienes
Diels–Alder reaction
Polymerization of dienes
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Reactions of Aromatics (Arenes)
Nitration [HNO3/H2SO4]
Chlorination [Cl
ALL THE BELOW REACTION IS GIVEN IN DETAIL IN THE LINK ABOVE
The Reaction Guide gives individual descriptions, examples, and mechanisms of more than 185 of the most common reactions encountered in undergraduate organic chemistry. Only members can access all of the full pages. Reactions highlighted in red are open-access.
Alkanes
Alkenes
Alkynes
Substitution (SN2)
Substitution (SN1)
Elimination Reactions
Alcohols and Thiols
Organometallics
Epoxides
Dienes
Aromatics (Arenes)
Aldehydes and Ketones
Carboxylic Acids
Esters
Acyl Halides
α,β-unsaturated alkenes
Amides
Nitriles
Miscellaneous
Alkanes
Free radical chlorination [hν, Cl2]
Free radical bromination [hν, Br2]
Allylic bromination [NBS]
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Alkenes
Addition of HCl
Addition of HBr
Addition of HI
Addition of H3O(+)
Chlorination [Cl2]
Bromination [Br2]
Iodination [I2]
Chlorohydrin formation [Cl2/H2O]
Bromohydrin formation [Br2/H2O]
Ether Formation [H+/ROH]
Oxymercuration [Hg(OAc)2/H2O]
Oxymercuration [Hg(OAc)2/ROH]
Hydroboration
Epoxidation [RCO3H]
Dihydroxylation [OsO4]
Dihydroxylation [KMnO4]
Cyclopropanation
Dichlorocyclopropanation
Ozonolysis (Reductive workup)
Ozonolysis (Oxidative workup)
Oxidative Cleavage [KMnO4]
Hydrogenation
Rearrangements (H shift)
Rearrangements (Alkyl shift)
Free Radical Addition of HBr
Sharpless Epoxidation
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Alkynes
Deprotonation (acetylide formation)
SN2 with alkyl halides
Partial reduction (Lindlar)
Partial reduction [Na/NH3]
Hydroboration
Oxymercuration
Addition of HCl, HBr, or HI (once)
Addition of HCl, HBr, or HI (twice)
Hydrogenation
Ozonolysis
Oxidative cleavage [KMnO4]
Alkyne formation via elimination
Halogenation [Cl2, Br2, I2]
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Substitution Reactions (SN2) [nucleophile in brackets]
Alcohol formation [HO(–)]
Alcohol formation [H2O]
Nitrile formation [CN(-)]
Thiol formation [HS(–)]
Ether formation [RO(–)] Williamson
Thioether formation [RS( –)]
Azides [N3(–)]
Ester formation [RCO2(–)]
Acetylide addition [RC≡C(–)]
Alkanes [Gilman reagents]
Alcohol formation [thru ether cleavage]
Ammonium salt formation [RNH2]
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Substitution Reactions (SN1) [nucleophile in brackets]
Alcohol formation [H2O]
Ether formation [ROH]
Alcohol formation [ether cleavage]
Alkyl chloride formation [HCl]
Alkyl bromide formation [HBr]
Alkyl iodide formation [HI]
SN1 w/ rearrangement [alkyl shift]
SN1 w/rearrangement [hydride shift]
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Elimination Reactions
E2: Alkenes from alkyl halides
Alkenes from alcohols [strong acid]
Alkenes from alcohols [POCl3]
E1: Alkenes from alkyl halides
E1 with rearrangement [alkyl shift]
Hoffmann Elimination
Alkyne formation via elimination
E1 with rearrangement [hydride shift]
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Reactions of Organometallics
Grignard formation [alkyl halides]
Grignard formation [alkenyl halides]
Reaction of Grignards with acid [H+]
Addition of Grignards to aldehydes
Addition of Grignards to ketones
Addition of Grignards to esters
Reaction of Grignards with CO2
Addition of Grignards to nitriles
Formation of organolithium reagents
Formation of Gilman reagents
SN2 with Gilman reagents
Addition of Gilman reagents to enones
Addition of Gilman to acyl halides
Heck Reaction
Suzuki Reaction
Stille Reaction
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Reactions of Epoxides
Epoxide opening [basic conditions]
Epoxide opening [acidic conditions]
Epoxide opening [diol formation]
Epoxide formation [from halohydrins]
Epoxide formation [from alkenes]
Sharpless Epoxidation of alkenes
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Reactions of Alcohols and Thiols
Deprotonation [alkoxide formation]
Protonation [onium ion formation]
Conversion to ethers [Williamson reaction]
Conversion to tosylates/mesylates
Conversion to alkyl chlorides [SOCl2]
Conversion to alkyl bromides [PBr3]
Oxidation to aldehydes [PCC]
Oxidation to ketones [PCC + others]
Oxidation to carboxylic acids [H2CrO4 + others]
Protection as silyl ethers
Thiol formation [SN2]
Thiol oxidation to disulfides
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Reactions of Dienes
Diels–Alder reaction
Polymerization of dienes
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Reactions of Aromatics (Arenes)
Nitration [HNO3/H2SO4]
Chlorination [Cl
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