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21 Cards in this Set
- Front
- Back
Alkene Reactions |
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Hydrohalogenation |
Reagents: HX (X = Br, Cl, F, etc.) + alkene —> haloalkane Mechanism notes: 1. Carbocation forms (most stable) 2. Nucleophile attacks carbocation Regiochemistry: Markovnikov Stereochemistry: syn. and anti. products form Extra notes: - watch for C+ rearrangements |
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Acid-catalyzed hydration or ether formation |
Reagents: H2SO4 + H2O or R-OH + H2SO4 Regiochemistry: Markovnikov Stereochemistry: syn. and anti. products form Extra notes: 1. H3O+ formation 2. Carbocation formation 3. Nucleophile attacks 4. Watch for C+ rearrangements |
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Halogenation |
Reagents: Br2 or Cl2 + DCM —> dihalide Regiochemistry: Anti-markovnikov Stereochemistry: anti. Extra notes: - bromonium or chloronium intermediate (no C+) - I2 and F2 don’t react! |
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Hydroboration |
Reagents: 1. BH3/THF 2. H2O2, OH-, H2O —> less substituted alcohol Regiochemsitry: Anti-markovnikov Stereochemistry: syn. |
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Halohydrin formation |
Reagents: Br2 or Cl2 + H2O —> halohydrin Mechanism notes: same mech. as Br2/DCM Regiochemistry: pseudo-Markovnikov b/c OH adds to more substituted C of alkene Stereochemistry: anti. Extra notes: - also works with R-OH instead of H2O |
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Expoxidation |
Reagents: MCPBA (or any peroxyacid) —> epoxide Regiochemistry: n/a Stereochemistry: syn. |
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Ozonolysis |
Reagents: 1. O3, -78°C 2. DMS —> ketone or aldehyde
Mechanism notes: - don't need to know mech. Regiochemistry: n/a Stereochemistry: n/a Extra notes: - every C=C —> C=O |
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Hydrogenation |
Reagents: H2 + Pd/C —> alkane
Mechanism notes: don't need to know mech. Regiochemistry: n/a Stereochemistry: syn. Extra notes: - Pd/C = catalyst (or in this case Pt - Platinum) - don't forget about sterochemistry |
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Alkyne Reactions |
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Hydrogenation (dissolving metal reduction) |
Reagents: Na/NH3 (l), -78°C —> trans alkene Regiochemistry: n/a Stereochemistry: n/a Extra notes: - trans alkene - does not work on terminal alkynes |
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Hydrogenation |
Reagents: H2 + Lindlar's catalyst alkyne —> cis alkene |
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Acid-catalyzed hydration (internal alkyne) |
Reagents: H2SO4 + H2O (internal alkyne —> ketone) Regiochemistry: Markovnikov Stereochemistry: n/a Extra notes: - ketone product - asymmetric internal alkynes —> 2 products |
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Acid-catalyzed hydration (terminal alkyne) |
Reagents: Hg2+, H2SO4, H2O (terminal alkyne —> ketone) Regiochemistry: Markonikov Stereochemistry: n/a Extra notes: - ketone product |
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HX alkyne addition |
Reagents: HX alkyne —> haloalkene Regiochemistry: Markovnikov Stereochemistry: n/a Extra notes: - 1 eq - add to carbocation - 2 eq - add to same carbon as first halogen |
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Halogen addition |
Reagents: Cl2 or Br2 Regiochemistry: n/a Stereochemistry: anti. Extra notes: Cl2 or Br2 |
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Hydroboration oxidation |
Reagents: 1. 9-BBN, THF 2. H2O2, H2O, NaOH Mechanism notes: - don't need to know mech. Regiochemistry: Anti-markovnikov Stereochemistry: n/a Extra notes: - terminal alkyne —> aldehyde - internal alkyne —> ketone |
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Diene Reactions |
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1, 2 addition |
Reagents: HX or H2SO4, H2O, conjugated (alternating double bonds) diene Stereochemistry: + E if you make a new asymmetric center (sp3 w/4 different groups) Extra notes: - to find which carbon is #1 (where the H goes) compare end carbons of diene and make #1 the less substituted one - if the two end carbons are equal make the carbon that leads to the more stable carbocation as #1 |
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1, 4 addition |
Reagents: HX or H2SO4, H2O, conjugated (alternating double bonds) diene Stereochemistry: + E if you make a new asymmetric center (sp3 w/4 different groups) Extra notes: - cold —> 1, 2 - hot —> most stable alkene (1, 2 or 1, 4) |
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Diels-Alder |
Reagents: diene + dienophile + ∆ (heat) Stereochemistry: - things on the dienophile with π e- are endo and down (on a dash) - things on carbons 1 + 4 of diene that are out are also down (on a dash) - "OUT-ENDO-CIS" - whatever is out on diene is cis to whatever is endo on the dienophile Extra notes: - diene must be s-cis - dienophile must be alkene or alkyne |