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 X2 CCl4 X Cl Br Addition NA Halohydrin formation X2 H2O X Cl Br Addition Markovnikov ish X adds to less OH adds to more subs C subs C Anti Addition each X adds on opposite sides of the C C plane Anti Addition X adds on one sides of the C C plane OH adds on the other side Bromohydrin formation NBS H2O DMSO Addition Hydration Acid Catalyzed H2O H3O cat H3PO4 H2SO4 Addition Markovnikov ish Br adds to less OH adds to more subs C subs C Anti Addition Br adds on one sides of the C C plane OH adds on the other side NA Markovnikov H adds to less subs C CHEM 227 C SERRANO LUGO OH adds to more subs C Cis Z gives syn cis dihalides wedge wedge or dash dash on a zigzag chain Trans E gives anti trans dihalides wedge dash or dash wedge on a zigzag chain Cis Z gives syn cis halohydrin wedge wedge or dash dash on a zigzag chain Trans E gives anti trans halohydrin wedge dash or dash wedge on a zigzag chain Cis Z gives syn cis halohydrin wedge wedge or dash dash on a zigzag chain Trans E gives anti trans halohydrin wedge dash or dash wedge on a zigzag chain NA X H X X HO X HO Br HO H en en en en en Starting Material Reaction Reagents Stereo specificity Product s General Mechanism Addition Hydration Oxymercuration Demercuration 1 Hg OAc 2 H2O 2 NaBH4 Ether formation Oxymercuration Demercuration 1 Hg OAc 2 ROH 2 NaBH4 Addition Hydration Hydroboration Oxidation 1 BH3 2 H2O2 NaOH Addition Mechanism for step 1 Markovnikov Anti Markovnikov 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 Markovnikov OH adds to less subs C H adds to more subs C Reduction Hydrogenation H2 Pd C Addition NA Oxidation Epoxidation mCPBA Addition NA Epoxidation Reaction of Bromohydrin and a strong base 1 Br2 H2O 2 NaOH or NaH Addition followed by Substitution Dihydroxylation Epoxidation followed by Acid Hydrolysis 1 mCPBA 2 H3O H2O Addition followed by Substitution NA NA CHEM 227 C SERRANO LUGO Anti Syn Stereochemistry Anti Addition H adds on one sides of the C C plane OH adds on the other side 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 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 NA NA NA NA NA NA en en en en en en en H H OH HO H RO H H O H O H HO OH Starting Material Reaction Reagents General Mechanism Markovnikov Anti Markovnikov Stereo specificity Product s Epoxide Opening with HX 1 mCPBA 2 HX X Cl Br I Addition followed by Substitution Dihydroxylation Oxidation with OsO4 1 OsO4 2 NaHSO3 H2O Addition Mechanism of step 1 Ozonolysis 2 Zn HOAc NA 1 O3 H2O 1 OsO4 2 NaHSO3 H2O 3 HIO4 KMnO4 H3O 1 O3 2 H2O2 Complicated Multiple Mechanisms Addition followed by Rearrange ment Addition followed by Rearrange ment Complicated Multiple Mechanisms X OH HO OH en en O O O H H OH O OH O O O O NA NA NA NA NA NA Anti Syn Stereochemistry Follows Syn Addition of Epoxide formation Substitution inverts the stereochemistry of the more substituted C Syn Addition Both OH add on the same side of the C C plane Dihydroxylation step follows Syn Addition Reaction with KMnO4 follows Syn Addition Reaction with KMnO4 follows Syn Addition Syn Addition Cyclopropane can only be formed if C C C bond are all on the same Subs that are Cis Z in the orig alkene will remain syn in the zigzag chain Subs that are Trans E in the orig alkene will remain anti in the zigzag NA chain NA NA NA NA CHCl3 KOH Addition NA CH2I2 Zn cu Addition Syn Addition Cyclopropane can only be formed if C C C bond are all on the same NA CHEM 227 C SERRANO LUGO 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 Same as the CHCl3 KOH rxn Cl Cl H H en en 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