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hydrohalogenation
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hydrohalogenation
hydrohalogenation
hydrohalogenation
hydrohalogenation
diels alder
s-cis
s-trans
diels alder
diels alder
diels alder
endo rule
substituents must be endo while the hydrogens must be exo
bicyclic diels alder
bicyclic diels alder
retro diels alder
electrocyclic
electrocyclic
electrocyclic
4e-
heat trans, light cis
4e-
heat trans, light cis
6e-
heat cis, light trans
6e-
heat cis, light trans
8e-
heat trans, light cis
sigmatropic rearrangement
when symmetrical, 3-3 is formed
sigmatropic rearrangement
sigmatropic rearrangement
allyl vinyl ether
aryl vinyl ether
sigmatropic rearrangement
hydrohalogenation
diels alder
bicyclic diels alder
10 annulene
non-aromatic
14 annulene
aromatic
2 annulene
antiaromatic
6 annulene
aromatic
8 annulene
nonaromatic
12 annulene
antiaromatic
antiaromatic
a ring is ________ if it’s aromatic in every way except it’s number of pi e- is a multiple of 4 (4n; 4, 8, 12, 16..)
aromatic
planar, fully conjugated, delocalized e-, 4n+2 pi e-, all carbons must be sp2 to be planar
ortho
1,2
meta
1,3
para
1,4
priority
aldehyde > ketone > alcohol > amine > alkyl
phenol
aniline
anisole
toluene
benzoic acid
benzaldehyde
o-xylene
m-xylene
p-xylene
acetophenone
benzophenone
styrene
oxidation
oxidation
oxidation
free-radical halogenation
substitution
substitution
elimination
ellimination
elimination
birch reduction
birch reduction
halogenation
halogenation
EAS mechanism
E = Cl or Br
B: = FeCl4 or FeBr4
halogenation
selefluor is used
halogenation
nitration
hydrosulfonation
reduction
friedel-craffs alkylation
limitations
any alkyl halide can be used (single bonds only)
impossible to stop at mono-alkylation (multiple substitutions)
wont react if theres a strong deactivator
rearrangement
rearrangement
friedel-acylation
friedel-acylation
sandmeyer
sandmeyer
sandmeyer
rearrangement
friedel acylation
reduction
nh2 to n2+
aromatic rxns
hydrolysis
activating groups
faster rxn, lone pair e- directly connected to benzene, neg or partial neg charge
ortho/para director
deactivating groups
slower rxn, pos or partiall pos charge
meta director
exception: halogens ortho/para deactivators
halogenation
sulfonation and halogenation
chlorination
sulfonation
ring priority
bromination
bromination
NAS (nucleophilic aromatic substitution)
NAS