The following are the summarized reactions of alkenes For reactions marked with an asterisk you need to know and understand the mechanism for the rest you only need to know everything else Starting Material Reaction Reagents Stereo specificity Product s Hydro halogenation HX X Cl Br I Addition NA NA Alkene Reaction Summary Sheet General Mechanism Anti Syn Stereochemistry Markovnikov Anti Markovnikov Markovnikov H adds to less subs C X adds to more subs C Halogenation Addition NA X2 CCl4 X Cl Br Anti Addition each X adds on opposite sides of the C C plane Halohydrin formation X2 H2O X Cl Br Addition Bromohydrin formation NBS H2O DMSO Addition Hydration Acid Catalyzed H2O H3O cat H3PO4 H2SO4 Addition Hydration Oxymercuration Demercuration 1 Hg OAc 2 H2O 2 NaBH4 Addition Markovnikov ish X adds to less OH adds to more subs C subs C Anti Addition X adds on one sides of the C C plane OH adds on the other side Markovnikov ish Br adds to less OH adds to more subs C subs C Markovnikov H adds to less subs C OH adds to more subs C Markovnikov H adds to less subs C OH adds to more subs C Anti Addition Br adds on one sides of the C C plane OH adds on the other side NA Anti Addition H adds on one sides of the C C plane OH adds on the other side CHEM 227 C SERRANO LUGO Cis Z gives syn cis dihalides Trans E gives anti trans dihalides Cis Z gives syn cis halohydrin Trans E gives anti trans halohydrin Both wedge dash or dash wedge on a ring Cis Z gives syn cis halohydrin Trans E gives anti trans halohydrin Both wedge dash or dash wedge on a ring NA NA en en en X H XX XOH BrOH HOH HOH Starting Material Reaction Reagents General Mechanism Stereo specificity Product s Markovnikov Anti Markovnikov 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 Ether formation Oxymercuration Demercuration 1 Hg OAc 2 ROH 2 NaBH4 Addition Hydration Hydroboration Oxidation 1 BH3 2 H2O2 NaOH Addition Mechanism of Step 1 Reduction Hydrogenation H2 Pd C Addition NA Oxidation Epoxidation mCPBA Addition NA Epoxidation Reaction of Bromohydrin and a strong base Dihydroxylation Epoxidation followed by Acid Hydrolysis 1 Br2 H2O 2 NaOH or NaH Addition followed by Substitution 1 mCPBA 2 H3O H2O Addition followed by Substitution Epoxide Opening with HX 1 mCPBA 2 HX X Cl Br I Addition followed by Substitution NA NA NA Anti Syn Stereochemistry Anti Addition H adds on one sides of the C C plane OH adds on the other side Syn Addition H and OH add on the same side of the C C plane Syn Addition Both H add on the same side of the C C plane Syn Addition Epoxide can only be formed if C O C bond are all on the same side Follows Anti Addition of Bromohydrin formation Substitution inverts the stereochemistry of the C bonded to OH Follows Syn Addition of Epoxide formation Substitution inverts the stereochemistry of the more substituted C Follows Syn Addition of Epoxide formation Substitution inverts the stereochemistry of the more substituted C CHEM 227 C SERRANO LUGO NA NA NA NA NA NA Subs that are Cis Z in the orig alkene will remain syn cis in the product Subs that are Trans E in the orig alkene will remain anti trans in the product en en en en en OR H H OH H H O O OH OH X OH Starting Material Reaction Reagents Stereo specificity Product s General Mechanism Markovnikov Anti Markovnikov Anti Syn Stereochemistry Dihydroxylation Oxidation with OsO4 1 OsO4 2 NaHSO3 H2O Addition Mechanism of Step 1 Syn Addition Both OH add on the same side of the C C plane NA NA NA NA NA Ozonolysis 2 Zn HOAc 1 O3 H2O Complicated Multiple Mechanisms 1 OsO4 2 NaHSO3 H2O 3 HIO4 KMnO4 H3O Addition followed by Rearrange ment Addition followed by Rearrange ment 1 O3 2 H2O2 Complicated Multiple Mechanisms Dihydroxylation followed by Oxidative Cleavage Oxidative Cleavage by Permanganate Oxidative Cleavage by Ozonolysis in Peroxide Cyclopropanation Reaction with Dichlorocarbene Cyclopropanation Reaction with Carbenoid aka Simmons Smith reaction CHCl3 KOH Addition NA NA Dihydroxylation step follows Syn Addition Reaction with KMnO4 follows Syn Addition Reaction with KMnO4 follows Syn Addition Syn Addition Cyclopropane can only be C C C bond are all on the formed if same Syn Addition Cyclopropane can only be C C C bond are all onhe formed if same NA NA NA NA NA NA en H H OH OH O O O O en OH OH O O O O Cl Cl CH2I2 Zn cu Addition NA NA en CHEM 227 C SERRANO LUGO