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28 Cards in this Set
- Front
- Back
Hydroboration |
1)Other reagents: BH3 in THF or B2H6 2) Other Bases: KOH |
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Oxymercuration |
Goes Through 3-memberd "mercurinium" ion. NaBH4 step removes the mercury. If -OH is used instead of H2O an ether will form. |
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Acid-catalyzed addition of H2O (Hydration) |
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Addition of HX |
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1)Bromination 2)Halohydrin Formation |
Water and alcohol solvents will for halohydrin but all others (CCl4, CHCl3, hexane) will give dibromide
Intermediate is a bromide bonded to both C |
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Chlorination |
Halohydrin is formed if water or alcohol is used as solvent |
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Epoxidation |
m-CPBA is commonly used for RCO3H
If H3O+, heat is added then epoxide is opened to give diol |
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Dihydroxylation |
1) Ocasioanlly a second reagent such as NaHSO3, H2S, or NA2S2O3 is used as a recant in the reaction
2) If heat or acid is mentioned the idol will be cleaved to form carbonyl compound |
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Hydrogenation
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Other metal catalysts include: Pt or Ni |
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Radical Addition of HBr
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Ozonolysis |
Reductive: Zn or DMS is used to reduce to isolate aldehyde Oxidative: H2O2 is used to obtain carboxylic acid instead of aldehyde (can also use KMnO4 and acid) |
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Cyclopropanation |
Can also use CHCl3, NaOH |
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Reductive Workup Mechanism |
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Oxidative Workup |
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3- Membered ring pathway (Br2/H2O2 to alkene) |
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Elimination of Hydrogen Halides |
Most substituted alkyne will form |
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Deprotonation |
Can also use strong base like n-BuLi, or RMgBr (Grignard reageants) |
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Reaction with Electrophile |
will react with alkyl halides in SN2 rxns |
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Hydrogenation |
Pt, Ni, Rh also can be used to go from alkyne to alkane |
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Partial Hydrogenation/ |
creates a cis-alkene through use of Pd, CaCO3 |
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Metal Ammonia Reduction |
Creates a trans-alkene |
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1) Addition of Hydrogen Bromide 2) Addition of Hydrogen Chloride |
A vinyl carbocation is formed as an intermediate in these creations. |
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Hydroboration |
Hydrboration on internal alkynes will give a mixture of ketones |
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Acid Catalyzed Hydration |
Tautomerization converts alkene into aldehyde/ketone |
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Oxymercuration |
The first intermediate is a cyclic ion (triangle between Hg and multi bond. |
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Chlorination |
First intermediate cyclic ion. First addition is trans |
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Ozonolysis |
If R=H then one product will be CO2 |
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Bromination |
First intermediate is cyclic ion. First addition is trans. |