FAT Orgo - Aromatic Compounds
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32 Terms
What must the shape of a molecule be in order to be aromatic
cyclic or polycyclic
What hybridization must the molecule be to be aromatic
all must be sp1 or sp2
Huckel’s rule
The number of pi electrons in a aromatic ring must be equal to 4n+2
double bonds and triple bonds count as two pi electrons
Under huckel’s rule, what do carbocations count as?
zero pi electrons
What must a ring be in order to be aromatic
planar
Antiaromatic molecules
a cyclic molecule with Sp2 or sp hybridized atoms
that doesnt meet huckel’s rule
When do lone pairs contribute to huckel’s rule
when it can form a double bond, DOES NOT COUNT WHEN A DOUBLE BOND IS RIGHT NEXT TO THE ATOM WITH THE ELECTRON
When do carbanions contribute to huckel’s rule
All the time, anions are counted in the 4n+2 when IT IS IN THE RING
Is octatetraene planar
no
How does aromaticity affect SN1 reactions?
If the carbocation formed when the LG takes off is aromatic, the SN1 reaction will be faster
How does aromaticity affect acidity?
If the conjugate base formed when the LG takes off is aromatic, the Acid will be more acidic
Benzylic carbons
Carbons with an H that are attached to a benzylic ring
side chain oxidation
as long as a benzoic carbon has an H attached to it, it can undergo the reaction
Clemsen and wolf kishner reactions
Turns COs into CH2
EAS reaction
An H is replaced with something else
EAS nitration
Sulfonation
Chlorination of bromination
Friedel crafts alkylation
Friedel crafts acylation
formylation
ortho, meta and para
ROMP, PMO
ortho/para directors
Electron donors
DOPE = Donors=ortho and para
Meta directors
Electron withrdrawers
W=M (withdrawers make you go meta)
Why are ortho/para directors ortho/para directors?
They juice up the ortho and para positions
Why are meta directors meta directors?
They suck electron density away from the ortho and para positions
What if there are two substituents that are fighting each other
the ortho-para director wins
Friedel crafts reactions and meta directors
they dont work on aromatic rings with strong meta directors on them
Diazonium salt
Diazonium salt
Nitrile hydrolysis
nitrille puls some h3o+ leads to carboxylic acid
Weak ortho/para donators
halogens, they withdraw as well to the point where normal benzne would be faster
