Markovnikov’s Rule
To generate the most stable intermediate, the proton (H) will be bonded to the carbon atom that already holds the greater number of hydrogens
-If there is a carbocation intermediate then you follow this rule
Anti-Markovnikov’s Rule
The proton (H) will be bonded to the carbon atom that holds the least number of hydrogens
Zaitsev’s Rule
If more than one elimination product is possible, the most substituted alkene is the major product (most stable)
Hofmann Product
When using bulky bases, the less substituted alkene is the major product
Sn1 Reaction
Sn2 Reaction
E1 Reaction
E2 Reaction
Dehydration of Alcohols
Starts with -OH and -H
Ends with an alkene
-Zaitsev’s rule
Hydrohalogenation
(adding H-X to alkenes)
Starts with a double bond
Ends with -H and -X
-Markovnikov’s rule
Hydration Reaction
Starts with alkene
Ends with -OH and -H
-Markovnikov’s rule
Alkoxymercuration
Starts with alkene and Hg(OAC)
Ends with -RO and -HgOAC
-markovnikov’s rule
Oxymercuration
Starts with alkene and Hg(OAC)
Ends with -OH and -HgOAC
-markovnikov’s rule
Hydroboration Reaction
Begin with alkene
Ends with -H and -BH2 added
-has transition state (must be shown)
-antimarkovnikovs rule
Halogen Addition
Halohydrin Reaction
Catalytic Hydrogenation
Begins with an alkene
Ends with the same molecule as an alkane
Addition of Carbenes
Dehydrogenation of Alkanes
Starts with -H and -H
Ends with an alkene
-Elimination reaction!
Addition of HBr (peroxide)
Starts with a double bond
Ends with a -Br and -H and Br radical
-antimarkovnikov’s rule
Demercuration
H replaces the HgOAC
-begins with oxymercuration/alkoxymercuration
Oxidation
-BH2 is replaced with -OH
-begins with hydroboration
-antimarkovnikov’s rule
Epoxidation
Syn hydroxylation
