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42 Cards in this Set
- Front
- Back
Add H2O to alkene
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Mark
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Reactivity of Electrophiles
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Best have:
1. Electrophilic carbon 2. Good leaving group |
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Strength of nucleophile rules
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1. Negative charge is good
2. Opposite of electronegativity 3. Polarizability is good BUT NOT FOR BASES 4. Hindered is bad; OPPOSITE FOR BASES |
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Leaving group rules
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1. Electron withdrawing
2. Stable after leaving (not a strong base) 3. Polarizable (to stabilize transition state |
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SN2 Stereochemistry
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Yes;
Walden Inversion |
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SN1 Stereochemistry
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Could do retention or inversion (50/50)
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E2 Stereochemistry
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Anti-coplanar, syn-coplanar stuff;
Anti-coplanar is favored |
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Add H2, Pt/Pd/Ni to alkene
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Add HOOH to alkene
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Oxidative Cleavage (O2)
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Add R-COOOH to alkene
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If you then add H3O+, makes a glycol (anti dihydroxylation)
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Add X2 to alkene
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Stereochemistry: anti
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Add X2, H2O to alkene
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Stereochemistry: anti
Mark on respect to OH |
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Add HX to alkene
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Cyclopropanation
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Free Radical Addition of HBr (mechanism)
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Anti-Mark (because that puts the free radical on the more stable carbon)
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How to get more E2, less SN2?
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Use bulky base
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How to get more Hoffmann product in Alkene synthesis
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Use bulky base
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Add Hg (OAc)2, H2O, NaBH4 to alkene
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Also works with alcohols
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Add BH3 to alkene
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Anti-Mark
Then add O (usually in form of H2O2/-OH/H2O) to make anti-Mark alcohol |
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Adding Br to a solution to test for DB
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No DB = color stays (no rxn)
DB = Clear (rxn) |
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Addition of carbenes to alkenes (:CR2)
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Making :CH2 from diazomethane
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Simmons-Smith Reaction
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Does addition of carbene
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McPBA
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Metachlorobenzoic acid;
Epoxidates alkenes; It with H3O+ works like cold, dilute KMnO4 (syn dihydroxylation) |
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Add OsO4, H2O2 to alkene
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Add KMnO4 to alkene
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1. Cold, dilute = syn dihydroxylation
2. Warm, concentrated = cleaves into two ketones |
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Add O3, Me2S to Alkene
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Oxidative Cleavage
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Olefin metathesis
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Make acetylide from R-CC-H
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Add NaNH2
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Acetylide + carbonyl group (ketone)
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Add another H+ to make a propanyl alcohol
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Synthesis of Alkyne?
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Eliminate vicinal or geminal dihalides using a base
1. KOH at 200 for internal 2. NaNH2 at 150, then H2O/H+ for terminal |
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Add A-B to alkyne
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Add H2, Pt to alkyne
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becomes alkane
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Add H2, Pd/BaSO4 to Alkyne
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Becomes cis alkene because it's poisoned
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Add NaNH3 to alkyne
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makes trans alkene
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Add X2 to alkyne
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Add HX to alkyne
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Mark for terminal alkynes
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Add HgSO4, H2SO4, H2O to alkyne
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Add R2BH to alkyne
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Add KMnO4 to alkyne
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Add KMnO4 and base to alkyne
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