Electrophilic Addition Reactions
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50 Terms
Markovnikov's rule
- electrophile → more sub carbon, + electrophile → less sub carbon
General EA Regiochemistry
Markovnikov's rule
General EA Intermediate
Carbocation (rearrangement possible)
General EA Stereoselectivity 1 chiral center
both enantiomers
General EA Stereoselectivity 2 chiral centers
both enantiomers + diasteromers
Acid catalyzed Hydration regiochemistry
Markovnikov's rule
Acid catalyzed Hydration intermediate
Carbocation (rearrangement possible)
Acid catalyzed Hydration stereochemistry
No control
Acid catalyzed Hydration mechanism
Acid deprotonated, water attacks carbocation, water deprotonated to regenerate acid
Cyclopropanation regiochemistry
None
Cyclopropanation stereoselectivity
Three-membered ring anti to other substituents
Cyclopropanation Intermediates
Three membered ring --> possible deprotonation
Epoxidation regiochemistry
None
Epoxidation intermediatees
Three membered ring --> possible deprotonation
Expoxidation stereselectivity
Ring anti to substituents
Halogenation regiochemistry
None (both substituents the same)
Halogenation intermediates
Cyclic
Halogenation stereoselectivity
Anti --> mix of enantiomers
Halogenation mechanism
Three-membered ring form with X+ then Sn2 like reaction
Halohydration regiochemistry
Markovnikov's Rule —> X at less sub, OH at more sub
Halohydration intermediates
Cyclic
Halohydration stereselectivity
Anti --> mix of enantiomers
Halohydration mechamism
Three membered ring with X+ then Sn2 like reaction
Halogenation of Alkynes regiochemistry
Markovnikov's rule
Halogenation of Alkynes intermediates
Carbocation (rearrangements possible)
Halogenation of Alkynes product
IF 1 equiv HX, alkene + 1 X added
IF 2 equiv HX, alkane + 2 X added
Hydration of Alkynes regiochemistry
Markovnikov's rule
Hydration of Alkynes intermediates
Carbocation then enol
Hydration of Alkynes final product
Ketone from tautomerization of enol
Hydration of Alkynes stereoselectivity
Enol = cis alkene
EA to dienes regiochemistry
Markovnikov's rule
Kinetic product
1,2 product, low heat
Thermodynamic product
1,4 product, high heat
EA to dienes intermediate
Carbocation --> resonance to form 1,4 product
EA to dienes stereoselectivity
Trans alkene
Hydrogenation of alkene regiochemistry
None
Hydrogenation of alkene mechanism
Concerted mechanism
Hydrogenation of alkene stereoselectivity
Syn
Hydrogenation of alkyne regiochemistry
None
Hydrogenation of alkyne mechanism
Concerted mechanism
Hydrogenation of alkyne stereoselectivity
Cis alkene
Hydrogenation of alkyne (NO LINDLAR) product
Alkane w/ syn selectivity
Hydroboration / oxidation regiochemistry
ANTI-Markovnikov --> OH to less sub, H to more sub
Hydroboration / oxidation intermediate
No carbocation --> not rearrangements
Hydroboration / oxidation stereoselectivity
Syn
Hydroboration / oxidation of alkyne intermediates
Cis alkene enol
Hydroboration / oxidation of alkyne final product
Ketone from tautomerization of enol
Oxymercuration / reduction regiochemistry
Markovnikov's rule
Oxymercuration / reduction intermediates
Cyclic —> no carbocation rearrangements
Oxymercuration / reduction stereoselectivity
First step = anti, final product = none