Synthetic Transformations

Addition of H and OH without rearrangement reagents

1. Hg(OAc₂), H₂O, THF

2. NaBH₄

Anti-Markovnikov Addition of H and OH Reagents

1. BH₃, THF

2. H₂O₂, NaOH, H₂O

Anti-Markovnikov addition of H and Br Reagents

HBr, ROOR, Heat

Markovnikov addition of H and X Reagents

HX, Cold and dark

Oxidation of an Alkene to an Epoxide reagents

MCPBA

Anti-Markovnikov Epoxide Ring Opening (basic) reagents

1. strong base

2. dilute acid

Markovnikov Epoxide Ring Opening (acidic) Reagents

H⁺, HOR

Markovnikov Addition of Br and OR to an alkene

Br₂, HOR

Cyclopropane Ring from an Alkene

CHCl₃, KOH (forms carbene)

Catalytic Hydrogenation

H₂ Pd/C

Selective Catalytic Hydrogenation of Alkyne (2 pathways)

H₂ with Lindlar or Ni₂B

Trans-addition of H₂

Na, NH₃

Oxidation of a 1º Alcohol to an Aldehyde

PCC

Oxidation of 2º Alcohol to a Ketone (4 pathways)

KMnO₄, Na₂Cr₂O₇/acid/water, CrO₃/acid/water, PCC

Oxidation of a 1º Alcohol or Aldehyde to a Carboxylic Acid

KMnO₄, Na₂Cr₂O₇/acid/water, CrO₃/acid/water

Syn Addition of Two OH Groups to a pi Bond

1. OsO₄

2. H₂O₂/NaHSO₃

Cleavage of a C=C Double Bond using Ozone (Ozonolysis)

1. O₃

2. Zn, acetic acid

Cleavage of a C=C Double Bond using Permaganate

1. KMnO₄ (hot)

2. H₃O⁺/H₂O

Markov. Addition of H 2O to an Alkyne

H₂O, H₂SO₄, HgSO₄

Anti-Markov. Addition of H₂O to an Alkyne

1. BH₃ THF

2. H2O2, NaOH, H2O

Deprotonation of an Alkyne

NaNH2

Nitrile Hydrolysis

H2O H2SO4

Halogenation of an alcohol (acid)

HX

Chlorination of an alcohol

SOCl2