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ochem exam 4

Alkene strong acid

HX, Markovnikov, carbocation intermediate, Hbr + peroxides = anti-Markov

Alkene, acid-catalyzed hydration

H2O / H2SO4, Markovnikov, rearrangements

Oxymercuation

1. Hg(OAc), THF/H2O

2. intermediate, NaBH4, OH-

Markovnikov, Anti addition

Alkene: Hydroboration-Oxidation

1. BH3, THF

2. H2O2, OH-

Anti-markov, syn addition, product + enan

Alkenes: Halonium ion

Br2 / Cl2 / I2, anti-addition, no RS

Halohydrin Formation

halogen, water, markovnikov (OH), anti-addition, product + enan

Hydrogenation

H2 + catalyst (Ni, Pd, Pt) + pressure, expands carbon chain (alkene to alkane), Syn addition, no RS

Alkene: SSCS

CH2I2, ring formation (party hat), syn addition, no RS

Alkene: Syn-dihydroxylation

O4 (lots of oxygen) COLD, (second step reagents depend on first step reagents), adds 2 OH, syn addition, no RS

oxidative cleavage

oxygen HEAT,

Alkyne: reduction