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Chapter 5 - Alkenes and Alkynes
| Term | Definition |
|---|---|
| Alkenes | carbon carbon double bonds; more reactive than alkanes; sometimes double bond acts as a base and attacks shit |
| terminal alkenes | lower bp |
| Trans-alkenes | higher mp and lower bp |
| Cis-alkenes | high bp cuz polar |
| Elimination rxns | synthesizing an alkene; loses halide and H, or water, to form double bond |
| E1 | two step intermediate, carbocation, first order substrate, good LG, weak nucleophile |
| E2 | one step, second order, strong nucleophile; removes proton and halide at same time to form double bond |
| Sn2 vs E2 | strong base favors E2 |
| catalytic hydrogenation | addition of H2 to an alkene to form alkane with the help of a metal |
| Electrophiles | electron seeking groups |
| Markovnikov's Rule | addition of something to the most substituted carbon in the double bond for stability |
| Addition of water to alkenes | only under acidic conditions, double bond attacks H+ from acid, then water attaches to cation then H+ is removed to form alcohol |
| Free Radical Additons | doesnt follow Mark's Rule. Halide binds to terminal carbon; halide binds then H+ is added |
| Hydroboration | when BH3 adds to less sterically hindered carbon of alkene then alcohol group replaces boron; BH3 and THF then H202 and base |
| cold KMnO4 Oxidation | produces diols (two OH groups added), syn/cis orientation |
| hot KMnO4 with OH- | forms COOH terminally or ketone and CO2 |
| Ozonolysis | 1.treating alkene with O3 and Zn gives 2 aldehydes 2. O3 and NaBH4 gives terminal alcohols |
| Peroxycarboxylic Acid | CH3CO3H or MCPBA give oxiranes/epoxides when combined with alkenes |
| Polymerization | creation of a long high molecular weight chain of repeating subunits |
| alkyne | hydrocarbon with triple bond |
| Synthesis alkyne | elimination of two molecules of HX but this is not practical adding an already existing triple bond to carbon skeleton; need strong base to remove H from alkyne to make it a nucleophile that can attack |
| Reduction Alkyne | 1. Lindlar's catalyst (BaSO4 and quinoline) give cis alkene 2. Ammonia (liquid) and Na give trans alkene |
| Free radicals | anti Mark's rule and X is added first |
| Ions | follow Mark's rule (most substituted carbon) and H+ added first |
| Alkyne O3 (Ozone) and KMnO4 rnx | both form COOH terminally |
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