Organic Chemistry | Synthetic Transformations

Markovnikov Addition of H and OH (Oxymercuration-Demercuration)

Name

1. Hg(OAc)2, H2O, THF (Solvent)

2. NaBH4

Regents

Markovnikov Addition of H and OR (Alkoxymercuration-Demercuration)

Name

1. Hg(OAc)2, HOR, THF (Solvent)

2. NaBH4

Regents

Anti-Markovnikov Addition of H and OH

Name

1. BH3, THF (Solvent)

2. H2O2, NaOH, Water (Solvent)

Regents

Anti-Markovnikov Addition of H and Br

Name

1. HBr, Peroxides (ROOR), Heat or Light

Regents

Markovnikov Addition of H and X (X = Cl, Br, or I)

Name

1. HX, Dark or Cold (No Peroxides)

Regents

Addition of Br2 to an Alkene

Name

Br2

Regents

Oxidation of an Alkene to an Epoxide

Name

1. MCPBA

Regents

Anti-Markovnikov Epoxide Epoxide Ring Opening (Basic Conditions)

Name

1. Strong Base (Nucleophile)

2. Dilute Acid

Regents

Markovnikov Epoxide Ring Opening (Acidic Conditions)

Name

1. H^+, HOR (R = H or Alkyl)

Regents

Markovnikov Addition of Br and OR to an Alkene

Name

1. Br2, HOR (R = H or Alkyl)

Regents

Cyclopropane Ring from an Alkene

Name

Path 1: CHCl3

Path 2: CH2I2, Zn(Cu)

Regents

Hydroboration-Oxidation

Name

1. BH3, THF

2. H2O2, NaOH, H2O

Regents

Catalytic Hydrogenation

Name

Path 1: H2, Pt^0

Path 2: Pd^0

Regents

Stereoselective Alkyne Reductions (#1)

Name

Path 1: H2/Pt

Path 2: Pd

Regents

Stereoselective Alkyne Reductions (#2)

Name

Path 1: H2/Ni2B

Path 2: H2/Lindlar Catalyst

Regents

Stereoselective Alkyne Reductions (#3)

Name

1. Na^0 (Sodium Metal), NH3 (Liquid Amonia)

Regents

Oxidation of 1^0 Alcohol to an Aldehyde

Name

PCC (Pyridinium Chlorochromate)

Regents

Oxidation of 2^0 Alcohol to a Ketone

Name

Path 1: KMnO4

Path 2: Na2Cr2O7/Acid/Water

Path 3: CrO3/Acid/Water

Regents

Oxidation of a 1^0 Alcohol or Aldehyde to a Carboxylic Acid

Name

Path 1: KMnO4

Path 2: Na2Cr2O7/Acid/Water

Path 3: CrO3/Acid/Water

Regents

Syn Addition of Two OH Groups to a π Bond

Name

1. OsO4

2. H2O2 or NaHSO3

Regents

Ozonolysis

Name

1. Ozone (O3)

2. Zn, Acetic Acid

Regents

Permanganate (MnO4^-1)

Name

1. KMnO4 (Hot)

2. H3O^+1/H2O

Regents

Markovnikov Addition of H and X to Alkyne (X = Cl, Br, or I)

Name

1. HX, Dark or Cold (No Peroxides)

2. HX (Excess), Dark or Cold (No Peroxides)

Regents

Addition of X2 to Alkyne (X=Cl or Br)

Name

1. X2

2. X2 (Excess)

Regents

Markovnikov Addition of H2O to an Alkyne

Name

1. H2O, H2SO4, HgSO4

Regents

Anti-Markovnikov Addition of H2O to an Alkyne

Name

1. BH3, THF

2. H2O2, NaOH, H2O

Regents

Deprotonation of an Alkyne

Name

1. NaNH2

Regents

Nitrile Hydrolysis

Name

1. H2O, H2SO4

2. Some Mechanism We Don't Know

Regents