5. Aromatic Compounds Flashcards
where does resonance come from in a aromatic compound
from the conjugated double bonds in the benzene
how many pi bonds are in an aromatic compound
4N + 2
N = whole number of rings
what is ortho nomenclature
2 attachments next to each other on the ring
what is meta nomenclature
2 attachments on ring with one space between the 2
what is para nomenclature
2 attachments on ring opposite each other
how is a mono/di-substituted aromatic compound prepared
electrophillic aromatic substitution
addition of E+ followed by elimination of H
what influences where the substituent goes when preparing a disubstituted aromatic compound
the first substituent on the ring controls whether the incoming electrophile is ortho/meta/para position
what kinds of activating and halogen deactivating substituents on the ring are ortho/para directing
strong/weak activating and deactivating
what is an example of a strongly activating substituent
-OH
-OR
what is an example of a weakly activating substituent
-CH3
what is an example of a deactivating substituent
-X
eg -F/Br/Cl/I
what do activating groups do to the e- density
pushes it into the ring
what do deactivating groups do to the e- density
pulls it out of the ring
why is ortho/para more liekly to occur than meta
o/p has 4 resonance structures while meta only has 3 so o/p more likely to occur
what kinds of activating/deactivating substituents on the ring are meta directing
strong/moderate deactivating
what are examples of strongly deactivating substituents
-NO-
what are examples of moderate deactivating substituents
-COH
-COR
what reagents or reactants are needed for an aromatic compound (benzene ring)
when it undergoes friedel crafts acylation
RXC=O + AlX3
(R & X attached to the C)
what is produced when an aromatic compound (benzene ring) undergoes friedel crafts acylation
adds RC=O onto aromatic ring
what is produced when RXC=O is added to AlX3 for aromatic compounds (benzene ring)
(R & X attached to the C)
produces aromatic ring with RC=O substituent
what reagents or reactants are needed for an aromatic compound (benzene ring)
when it undergoes friedel crafts alkylation
RX + AlX3
for what types of alkanes can friedel crafts alkylation occur
small alkanes
what is produced when RX is added to AlX3 for aromatic compounds (benzene ring)
friedel crafts alkylation
produces aromatic ring with R attached
what kind of substitution are friedels craft acylation/alkylation
mono substitution
how do you go from a benzene ring no substituents to a X as the only substituent on the benzene ring
what reagents or reactants are needed
+X2/FeX3
where X = Cl or Br
how do you go from a benzene ring no substituents to a RC=O as the only substituent on the benzene ring
what reagents or reactants are needed
+RXC=O/AlX3
(R & X attached to the C)
how do you go from a benzene ring no substituents to a CH3 as the only substituent on the benzene ring
what reagents or reactants are needed
+CH3X/AlX3
how do you go from a benzene ring no substituents to a NO2 as the only substituent on the benzene ring
what reagents or reactants are needed
+HNO3/H2SO4
what happens when you
+RXC=O/AlX3
to a non substituted benzene ring (what is produced)
-RC=O added onto the ring
what happens when you
+X2/FeX3
to a non substituted benzene ring
-X added onto the ring
what happens when you
+CH3X/AlX3
to a non substituted benzene ring
-CH3 added onto the ring
what happens when you
+HNO3/H2SO4
to a non substituted benzene ring
-NO2 added onto the ring
how do you go from a benzene ring with -NO2 attached as the only substituent on the benzene ring to a -NH2 as the only substituent on the benzene ring
what reagents or reactants are needed
+Fe/H+ & OH-
how do you go from a benzene ring with -NH2 attached as the only substituent on the benzene ring to a -N(triple bond)N as the only substituent on the benzene ring
what reagents or reactants are needed
+HNO2/0 degrees celsius
how do you go from a benzene ring with -N(triple bond)N attached as the only substituent on the benzene ring to a -OH as the only substituent on the benzene ring
what reagents or reactants are needed
+H3O+
how do you go from a benzene ring with –N(triple bond)N attached as the only substituent on the benzene ring to a -CN as the only substituent on the benzene ring
what reagents or reactants are needed
+CuCN
how do you go from a benzene ring with -CN attached as the only substituent on the benzene ring to a -COOH as the only substituent on the benzene ring
what reagents or reactants are needed
+H3O+
how do you go from a benzene ring with -COOH attached as the only substituent on the benzene ring to a -ClC=O as the only substituent on the benzene ring
what reagents or reactants are needed
+SOCl2
what happens when you
+Fe/H+ & OH-
to a benzene ring with a -NO2 attached
-NH2 replaces the -NO2
what happens when you
+HNO2/0 degrees celsius
to a benzene ring with a -NH2 attached
-N(triple bond)N replaces the -NH2
what happens when you
+H3O+
to a benzene ring with a -N(triple bond)N attached
-OH replaces the -N(triple bond)N
what happens when you
+CuCN
to a benzene ring with a -N(triple bond)N attached
-CN replaces the -N(triple bond)N
what happens when you
+H3O+
to a benzene ring with a -CN attached
-COOH replaces the -CN
what happens when you
+SOCl2
to a benzene ring with a -OH attached
-ClC=O replaces the -COOH
