The following are the summarized reactions of alkynes This table does not include the reactions that produces alkynes which are included in the exam Starting Material Reaction Reagents Alkene Reaction Summary Sheet General Mechanism Markovnikov Anti Markovnikov Anti Syn Stereochemistry Hydro halogenation HX X Cl Br I Addition Markovnikov H adds to less subs C X adds to more subs C Halogenation Addition NA X2 CCl4 X Cl Br Hydration Oxymercuration Demercuration Hydration Hydroboration Oxidation Reduction Hydrogenation Reduction Cis Reduction Trans Hydrogenation HgSO4 H2SO4 H2O Addition 1 BH3 2 H2O2 NaOH Addition H2 Pd C Addition H2 Li or Na NH3 Addition Addition single and two electron mechanism Complicated Multiple Mechanisms Ozonolysis 1 O3 2 Zn HOAc H2O Oxidative Cleavage using KMnO4 KMnO4 Addition Hydrogenation Lindlar catalyst Markovnikov H adds to less subs C OH adds to more subs C Anti Markovnikov OH adds to less subs C H adds to more subs C NA NA NA NA NA NA Anti Addition each X adds on opposite sides of the triple and double bond Gives trans dihalides with the 1st equiv Syn Addition but inconsequential Syn Addition but inconsequential since final product is an alkane Syn Addition Trans Addition NA NA NA NA NA Product s XX XX X O O X H R O O OH OH CO2 CO2 Acetylide formation followed If you use a 2o or 3o RX then elimination reaction will be preferred over substitution followed by substitution NaNH2 RX 1o by alkylation alkyne Deprotonation of terminal CHEM 227 C SERRANO LUGO