Reaction Mechanisms

HX (mark)

-mark

-halide is added to most substituted side & H is added to least substituted side

HX & ROOR (Peroxide)

-anti-mark

-halid is added to least substituted side & H is added to most substituted side

X2 & CCl4 (or CH2Cl2)

-anti

-halides have diff stereochemistry

X2 & H2O

-anti & mark

-diff stereochemistry & halide is placed on less substituted & OH is on more substituted

H2SO4 & heat

adds internal bonds & removes OH

POCl3 & heat

adds external bonds & removes OH

H3O+

-mark

-DB breaks, adds OH to most sub. carbon & H to least sub

1. Hg(OAc)2, H2O

2. NaBH4

-mark & anti

-OH added to most substituted side & H added to least substituted side (diff stereochemistry)

1. Hg(OAc)2, CH3OH

2. NaBH4

-mark & anti

-OCH3 added to most substituted side & H added to least substituted side (diff stereochemistry)

1. BH3/THF

2. H2O2/OH

-anti-mark & syn

-add H to most substituted side & OH to least substituted side (same stereochemistry)

H2 & Pd/Pt/Ni

-syn

2 hydrogens added (same stereo)

OsO4 & H2O2

syn addition of OH and OH

KMnO4 (cold, basic)

syn addition of OH and OH

CH3CO3H & H2O

anti addition of OH & OH

1) O3/CH2Cl2

2) (CH3)2S ( can also use Zn/acetic acid)

forms 2 carbonyls (ketone- RR, formaldehyde-HH, aldehyde-RH)

warm KMnO4

can form 2 carbonyls or 1 carbonyl + byproducts

(ketone-RR, carboxylic acid- ROH, & CO2/H2O)

CH2N2 & heat

-Syn

-DB breaks & connects to CH2 (same stereochem for CH2)

CH2I2 & Zn(Cu)

-Syn

-DB breaks & connects to CH2 (stereochem not on CH2)

mCPBA & CH2Cl2

-syn

-DB breaks & connects to O (same stereo)

H+ & H2O

-anti

-O bond breaks & 2 OH form (diff stereo)

CHCl3 & KOH

DB breaks & connects to CCl2

1) OH-

2) H+

-anti

-O bond breaks & 2 OH form (diff stereo)

CHBr3 & KOH

DB breaks & connects to CBr2

NaOH (any group 1 metal)

removes halide & creates double bond

NaI or KI & Acetone

removes halides & creates double bond