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24 Cards in this Set

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Hydrohalogenation


-Markovnikov Addition


-Racemic Mixture


-Susceptible to carbocation rearrangement

Acid Catalyzed Hydration


-Markovnikov


-Racemic


-Carbocation Rearrangement

Oxymercuration-Demercuration


-Markovnikov


-No Carbocation Rearrangement

Hydroboration Oxidation


-Anti-Markovnikov


-Syn Addition

Catalytic Hydrogenation


-Syn Addition

Halogenation


-Anti Addition

Halohydrin Formation


-OH group at more substituted position


-Anti Addition

Anti Dihydroxylation


-Epoxide intermediate


-MCPBA is a common peroxy acid

Syn Dihydroxylation


-OsO4 acts as a catalyst when paired with a co-oxidant

Ozonolysis

Preparation of Alkynes


-E2 reaction with a strong base (NaNH2)

Hydrohalogenation (Excess)


-Markovnikov

Hydrohalogenation


-Markovnikov

Acid-Catalyzed Hydration


-Markovnikov


-Acid-catalyzed keto-enol tautomerization favors ketone product

Hydroboration Oxidation


-Anti-Markovnikov


-Disiamylborane and 9-BBN are examples of R2BH


-Undergoes base-catalyzed tautomerization

Halogenation


-Anti Addition

Ozonolysis


-Forms carboxylic acids/carbon dioxide

Alkylation

Catalytic Hydrogenation

Catalytic Hydrogenation (Poisoned Catalyst)


-Lindlars Catalyst: Pd prepared with CaCO3


-Syn Addition

Dissolving Metal Reduction


-Anti Addition

Radical Bromimation


-Occurs at more substituted position


-Racemic

Anti-Markovnikov Addition of HBr


-Requires trace amounts of alkyl peroxide

Allylic Radical Bromimation


-Avoids the addition of Br2 across the pi bond


-NBS is an alternative source of radical bromine