Organic Chem I Exam 3 (Ch. 7 & 8)

Reactions

HBr

reagent used in hydrohalogenation (Markov)

1. HBr

2. ROOR

reagent used in hydrohalogenation (Anti-Markov)

H₃O⁺ or diluted H₂SO₄

reagents used in acid-catalyzed hydration

1. Hg(OAc)₂, H₂O

2. NaBH₄

reagents used in oxymercuration-demercuration

1. BH₃*THF

2. H₂O₂, NaOH

reagents used in hydroboration-oxidation

1. H₂

2. Pt, Ni, Pd

reagents used in catalytic hydrogenation

Br₂

reagent used in halogenation

1. O₃

2. DMS

reagents used in ozonolysis (oxidative cleavage)

1. Br₂

2. H₂O

reagents used in halohydrin formation

1. MCPBA or RCO₃H

2. H₃O⁺

reagents used in anti-dihydroxylation

1. OsO₄, pyridines

2. NaHSO₃, H₂O

OR

1. KMnO₄

2. NaOH, cold

reagents used in syn-dihydroxylation

Markovnikov

goes to MORE substituted carbon

Anti-Markovnikov

goes to LESS substituted carbon

Hydrohalogenation (Markov)

Hydrohalogenation (Anti-Markov)

Acid-cat hydration (Markov only, can rearrange)

Oxymercuration-demercuration (Markov, can’t rearrange)

Hydroboration (Anti-Markov only)

Hydroboration (syn addition)

Syn addition

both wedges or both dashes

Anti addition

one wedge, one dash

Anti addition

halides added to opposite ends of the double bond

Catalytic hydrogenation

Catalytic hydrogenation (syn add of H₂)

Halogenation (anti addition)

Halogenation (anti addition)

Ozonolysis

Ozonolysis

Halohydrin formation

Anti addition of OH & Br. OH goes to Markov position, Br to Anti-Markov.

Halohydrin formation

Anti-Dihydroxylation

2 OHs added, anti addition (one wedge, one dash)

Anti-Dihydroxylation

Syn-Dihydroxylation

2 OHs added, syn addition

Syn-Dihydroxylation

Hydrohalogenation mechanism

Acid-catalyzed hydration mechanism

Hydroboration mechanism

Hydroboration mechanism

Halogenation mechanism

Halohydrin formation mechanism

Anti-dihydroxylation mechanism

Anti-dihydroxylation mechanism (acid-catalyzed opening of epoxide)

Syn-dihydroxylation mechanism

Hydrohalogenation (Markov)

HBr