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Chapter 5 - Alkenes and Alkynes

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
Created by: JaeBae4444