Aromatic Hydrocarbon Reactions Flashcards
characterized by the presence of the benzene ring.
aromatic hydrocarbons
six-membered ring with alternating single and double bond.
benzene ring
unlike the typical alkene, benzene rings are typically stable due to presence of pi electrons that undergo what
electron delocalization
Aromatic compounds need to satisfy these requirements:
- cyclic
- alternating single and double bond or all carbons are sp2 hybridized
- planar
- follow Huckel’s rule
state that total number of pi electrons of a aromatic ring is 4n + 2 (2, 6, 10, 14…)
Huckel’s rule
happens due to the presence of fully conjugated unsaturated ring systems
aromatic
the benzene is entirely this around the entire molecule
delocalized
benzene has this around the ring
partial pi electron density
determine if the compound is an aromatic compound
grade yourself accordingly
undergo electrophilic aromatic substitution
aromatic compounds
in electrophilic
aromatic substitution, this will attack
the electrophile and substitute the
electrophile for one of the H atoms
pi electrons
this is retained after
electrophilic aromatic substitution
aromaticity
facilitates electrophilic aromatic substitution
lewis acid catalyst
enumerate the strongly activating directing groups
NH2
OH
OCH3
NH-C(=O)-CH3
enumerate the weakly activating directing groups
CH3
C6H5
H
Atoms or groups that make the benzene molecule more reactive by increasing the ring’s electron density
activating groups
ortho para directors include
-H
-F
-Cl
-Br
-I
m-directors include
O=C-H (aldehyde)
O=C-OCH3 (ester)
O=C-OH (carboxylic acid)
-SO3H (sulfonic acid)
-CN
-NO2
-NR3
illustrate the nitration reaction in aromatic hydrocarbons
grade yourself accordingly
illustrate the bromination of aromatic hydrocarbons
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illustrate the chlorination (Cl2) of aromatic hydrocarbons
grade yourself accordingly
illustrate the sulfonation of aromatic hydrocarbons
grade yourself accordingly
illustrate the alkylation (Ch3CH2Cl) of aromatic hydrocarbons
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illustrate the alkylation of Ch3CH=Cl2
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illustrate the acylation of aromatic
grade youself accordingly
illustrate the deuteration of aromatic hydrocarbons
grade yourself accordingly
