Chapter 5 - Alkenes and Alkynes
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| Alkenes | carbon carbon double bonds; more reactive than alkanes; sometimes double bond acts as a base and attacks shit
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| terminal alkenes | lower bp
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| Trans-alkenes | higher mp and lower bp
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| Cis-alkenes | high bp cuz polar
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| Elimination rxns | synthesizing an alkene; loses halide and H, or water, to form double bond
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| E1 | two step intermediate, carbocation, first order substrate, good LG, weak nucleophile
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| E2 | one step, second order, strong nucleophile; removes proton and halide at same time to form double bond
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| Sn2 vs E2 | strong base favors E2
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| catalytic hydrogenation | addition of H2 to an alkene to form alkane with the help of a metal
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| Electrophiles | electron seeking groups
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| Markovnikov's Rule | addition of something to the most substituted carbon in the double bond for stability
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| 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
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| Free Radical Additons | doesnt follow Mark's Rule. Halide binds to terminal carbon; halide binds then H+ is added
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| Hydroboration | when BH3 adds to less sterically hindered carbon of alkene then alcohol group replaces boron; BH3 and THF then H202 and base
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| cold KMnO4 Oxidation | produces diols (two OH groups added), syn/cis orientation
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| hot KMnO4 with OH- | forms COOH terminally or ketone and CO2
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| Ozonolysis | 1.treating alkene with O3 and Zn gives 2 aldehydes
2. O3 and NaBH4 gives terminal alcohols
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| Peroxycarboxylic Acid | CH3CO3H or MCPBA give oxiranes/epoxides when combined with alkenes
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| Polymerization | creation of a long high molecular weight chain of repeating subunits
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| alkyne | hydrocarbon with triple bond
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| 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
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| Reduction Alkyne | 1. Lindlar's catalyst (BaSO4 and quinoline) give cis alkene
2. Ammonia (liquid) and Na give trans alkene
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| Free radicals | anti Mark's rule and X is added first
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| Ions | follow Mark's rule (most substituted carbon) and H+ added first
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| Alkyne O3 (Ozone) and KMnO4 rnx | both form COOH terminally
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