8. Electrophilic Alkenes

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Chemistry Flashcards on 8. Electrophilic Alkenes, created by John Rivada on 22/04/2019.
John Rivada
Flashcards by John Rivada, updated more than 1 year ago
John Rivada
Created by John Rivada about 5 years ago
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Question Answer
Where on this compound is the hard El site and where is the soft El site? 2 (carbonyl) = hard El 4 (alkene) = soft El
Mechanism for stoichiometric anionic Nu- conjugate addition
Mechanism for catalytic anionic Nu- and stoichiometric Nu-H conjugate addition
Mechanism for catalytic H+ and stoichiometric Nu-H conjugate addition
Mechanism for stoichiometric Nu-H with no catayltic acid or base conjugate addition
Excess amine
Excess ester
Give mechanism
Give mechanism
Between 1,4 and 1,2 addition, which is the kinetic product and which is the thermodynamic product? 1,2 addition is kinetic 1,4 addition is thermodynamic
Scale from 1,4 to 1,2 addition Left is 1,2 and right is 1,4
How does the kind of allylic structure (1°, 2°, 3°) affect whether 1,4 or 1,2 addition occurs? 1° - 1,4 addition 2° - in the middle 3° - 1,2 addition
If you want to force a reaction to do 1,4 addition, what should you use? Copper(I) !!!!
Why is alkyne considered a dummy ligand? Once you add to a cuprate it doesn't come off!!!!
What' so fancy about H2O2? The LG is on the Nu!!! WOAHHHHHHHHHH
What kind of electrophiles can you use for an electrophilic aromatic substitution? Bromination (Br2 + FeBr3) Nitration (HNO3 + h2SO4) Sulfonation (H2SO4)!
What is friedal-crafts alkylation? So you got R-X and then AlX3 AlX3 pulls X from R -X R+ which then gets attacked by your benzene which and proceeds like electrophilic aromatic substitution
What is friedal crasts acylation? The same as alkylation but theres a carbonyl group present
Friedal-Crafts mechanism **
What two things do you need on your aromatic ring for SnAr to occur? F substitent and another EWG (carbonyl, sulfone, sulfoxide, nitro)
SnAr mechanism **
ortho/meta/para directing groups **
Hono mechanism **
benzyne mehcnaism **
sn2'
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