Organic Reactions I

Addition of HX to Alkene

Reagents: HX, Solvents: Ether, Stereochemistry: mix, Regiochemistry: Markonikov

Addition of Halogens Cl2 and Br2 (Alkenes)

Reagents: Cl2 or Br2, Solvents: CH2Cl2, Stereochemistry: anti, Regiochemistry: none

Halohydrin Formation (Alkenes)

Reagents: X2 or NBS, Solvents: H2O or H2O, DMSO, Stereochemistry: anti, Regiochemistry: Markonikov

Addition of water by oxymercuration-demercuration (Alkenes)

Reagents: 1. Hg(Oac)2, 2. NaBH4, Solvents: H2O and THF, Stereochemistry: anti, Regiochemistry: Markonikov 

Addition of water by hydroboration-oxidation (Alkenes)

Reagents: 1. BH3, 2. H2O2, OH-, Solvents: THF, Stereochemistry: syn, Regiochemistry: Anti-Markonikov

Catalytic Hydrogenation (Alkenes)

Reagents: H2, Solvents: Pd/C or PtO2, Stereochemistry: syn, Regiochemistry: none

Epoxidation with Peroxyacid (Alkenes)

Reagents: MCPBA, Solvents: CH2Cl2, Stereochemistry: syn, Regiochemistry: none

Hydration of Alkenes (general)

Reagents: H2SO4/H3PO4 and H2O, Solvents: heat, Stereochemistry: mix, Regiochemistry: Markonikov

Dehydrohalogenation of Alkyl Halide (Alkenes)

Reagents: Base, Solvents: CH3CH2OH, Stereochemistry: none, Regiochemistry: none

Dehydration of Alcohol (Alkenes) 

Reagents: H2SO4/H3PO4, heat, Solvents: none, Stereochemistry: none, Regiochemistry: none

Hydroxylation of Epoxides

Reagents: H3O+, Epoxide, Solvents: H2O, Stereochemistry: trans, Regiochemistry: Markonikov

Hydroxylation of Alkenes

Reagents: 1. OsO4, 2. NaHSO3-, Solvents: H2O, Stereochemistry: syn, Regiochemistry: none

Carbenes to Cyclopropane (Alkenes)

Reagents: KOH, Solvents: CHCl3, Stereochemistry: none, Regiochemistry: none

Carbenes to Cyclopropane in Alkenes: Simmons-Smith Reaction

Reagents: Zn(Cu), CH2I2, Solvents: Ether, Stereochemistry: none, Regiochemistry: none

Oxidative Cleavage of Alkenes: Ozonolysis

Reagents: 1. O3, 2. Zn/H3O+, Solvents: CH3COOH, Stereochemistry: none, Regiochemistry: none

Oxidative Cleavage of Alkenes: KMnO4 (internal alkene)

Reagents: KMnO4, H3O+, Solvents: Acidic solution, Stereochemistry: none, Regiochemistry: none

Oxidative Cleavage of Alkenes: KMnO4 (terminal alkene) to make Carboxyllic Acid and CO2

Reagents: KMnO4, H3O+, Solvents: Acidic solution, Stereochemistry: none, Regiochemistry: none

Cleavage of 1,2 Diols

Reagents: HIO4, Solvents: H2O, Stereochemistry: none, Regiochemistry: none

Dehydrohalogenation of Dihalides (Alkynes)

Reagents: 2 KOH or 2 NaNH2, Solvents: ethanol or NH3, Stereochemistry: none, Regiochemistry: none

Dehydrohalogenation of Dihalides (Alkynes)

Reagents: KOH or NaNH2, Solvents: ethanol or NH3, Stereochemistry: none, Regiochemistry: none

Addition of HCI and HBR (Alkynes)

Reagents: HX, Solvents: ether, Stereochemistry: Anti normally, Regiochemistry: Markonikov

Addition of X2 (Alkynes)

Reagents: X2, Solvents: CH2Cl2, Stereochemistry: Anti normally, Regiochemistry: Markonikov

Hydration of Alkynes

Reagents: H2SO4, H2O, Solvents: HgSO4, Stereochemistry: none, Regiochemistry: Markonikov

Hydration of Alkynes

Reagents: 1. BH3, 2. H2O2, Solvents: THF, Stereochemistry: none, Regiochemistry: Anti-Markonikov

Hydrogenation of Alkynes

Reagents: H2, Solvents: Lindlar Catalyst, Stereochemistry: cis, Regiochemistry: none

Hydrogenation of Alkynes

Reagents: Li, Solvents: NH3, Stereochemistry: trans, Regiochemistry: none

Conversion into Acetylide Anions to Polymerization

Reagents: NaNH2, Solvents: CHnX, NH3, Stereochemistry: None, Regiochemistry: none

Allylic Halogenation

Reagents: NBS, Solvents: hv, CCl4, Stereochemistry: none, Regiochemistry: none

Alcohols to Halides (general)

Reagents: HX, Solvents: Ether, Stereochemistry: none, Regiochemistry: none

Reaction of Primary and Secondary Alcohols to Halides

Reagents: SOCl2, Solvents: Pyridine, Stereochemistry: none, Regiochemistry: none

Reaction of Primary and Secondary Alcohols to Halides

Reagents: PBr3, Solvents: Ether, Stereochemistry: none, Regiochemistry: none

Reaction of Primary and Secondary Alcohols to Halides

Reagents: HF, Solvents: Pyridine, Stereochemistry: none, Regiochemistry: none

Formation of Grignard Reagents (Organomagnesium)

Reagents: Mg, Solvents: ether, Stereochemistry: none, Regiochemistry: none

Formation of Gilman Reagents (Diorganocopper)

Reagents: 2Li, Solvents: Pentane, Stereochemistry: none, Regiochemistry: none

Formation of Gilman Reagents 2

Reagents: Ether, Solvents: None, Stereochemistry: none, Regiochemistry: none

Organometallic Coupling (Diorganocopper Reaction)

Reagents: Ether, Solvents: None, Stereochemistry: none, Regiochemistry: none

Palladium-Catalyzed Suzuki-Miyaura

Reagents: Pd(PPh3)4, Solvents: CaCO3, THF, Stereochemistry: none, Regiochemistry: none