aromatic compounds Flashcards
benzene undergoes mainly
substitution
what is the simplest aromatic hydrocarbon
benzene
what is the molecular formula of benzene
C6H6
in the kekule structure, do the single and double bond alternate around the ring
yes
what is a highly unsaturated molecule
benzene
what is the positive test for unsaturated benzene
if the orange red colour of bromine disappears/ decolorizes
what cant take place when the single and double bonds exchange position around the ring of the kekule structure
the reactions of alkanes cant take place
do the rings move slowly or rapidly around the single and double bonds exchange position around the ring of the kekule structure
rapidly
what is more stable than either of its contributing kekule structure
benzene
in the orbital model for benzene, each carbon atom is what hybridized
sp2
what is the angle of the orbital model for benzene
H-C-C
C-C-C
120 degree
in the delocalized pi cloud of benzene, what do the circle emphasize
it emphasize that the electrons are distributed evenly around the ring
the kekule structure is what kind of form
resonance form
the benzene ring is what kind of form
simplified depiction
is the double bonds in benzene are in fixed positions and why
no because the electrons are distributed evenly around the ring
what is ‘o’
ortho
what is ‘m’
meta
what is ‘p’
para
‘o’ is on what carbon
2&6
‘m’ is on what carbon
3&5
‘p’ is on what carbon
4
how to name benzene (from my understanding)
prefix + substituent + benzene
what is classified as arenes
aromatic compounds
aromatic carbons is classified as
arenes
Ar
aryl group
R
alkyl group
what is the removal of hydrogen from aromatic ring
aryl group
what is the removal of one hydrogen from an alkane chain (from an alkane substituent)
alkyl group
define arly group
the removal of hydrogen from aromatic ring
define alkyl group
the removal of one hydrogen from an alkane chain (from an alkane substituent)
what are the 2 aromatic compounds
phenyl group
benzyl group
what is formed by removing one H from benzene
phenyl group
what is the molecular formula of phenyl group
C6H5
what is the molecular formula of benzyl group
C6H5CH2
benzene undergoes substitution reaction but it reacts slowly with
Br2
which structure has a cyclic planar
benzene
what is the C-C bond length of benzene
1.39 A
benzene is intermediate to
c-c & c=c
what is the extra stability associated with aromatic compound
aromaticity
what are the requirements to know that it is an aromatic compound
cyclic
planar
fully conjugated
contain 4n+2pi electrons
in benzene, are all C-C bonds the same
yes they are resonance
in benzene, what bonds are in equal length
C-C
what is the measure of the extra stability of the cyclic conjugated system compared to corresponding no. of isolated double bonds
resonance energy
what are the 2 effects of the large resonance stabilization energy
stabilization energy lost when an electrophile adds to the ring
stabilization energy regained when an electrophile adds to the ring intermediate carbocation loses a H+
in the effect of large resonance stabilization energy, when energy is lost when an electrophile adds to the ring. hence, what do we need to use
a catalyst (much stronger electrophiles)
in the effect of large resonance stabilization energy, when energy is regained when an electrophile adds to the ring intermediate carbocation loses a H+. this results in
substitution
what has a cyclic conjugated with 6pi electrons
benzene
what are the 6 common substitution reactions in electrophilic aromatic substitution
chlorination
bromination
nitration
sulfonation
alkylation
acylation
EAS
electrophilic aromatic substitution
do all EAS have the same mechanism
yes
the reaction rates of EAS depends on the attack of…
electrophile on the benzene ring
in the reaction rates of EAS,
groups that has a high charge density..
speed up reaction
in the reaction rates of EAS,
groups that has a low charge density..
slow down reaction
EDG
electron donating group
EWG
electron withdrawing group
is o,p-directing EDG or EWG
EDG
is m-directing EDG or EWG
EWG
EDG activates or deactivates the ring
activate
EWG activates or deactivates the ring
deactivate
EDG activate the ring to stabilize or destabilizing the wheland intermediate
stabilize
EWG activate the ring to stabilize or destabilizing the wheland intermediate
destabilizing
all alkyl group are what kind of directors
ortho, para directors
ortho and para directors has any substituent that has…
lone pairs of electrons
meta directors has any substituent that has a…
positively polarized atom (delta plus, delta minus) tat is directly attached to the ring
in the synthesis of organic compounds, you need to know the
reactions and their directing effects
what is the production of new mol. needed for drugs
the synthesis of organic compounds
in the synthesis of organic compound,
what works backward from the products
retrosynthesis
in the synthesis of organic compound,
what is the production process
synthesis
what do you call a multiple fused rings
polycyclic aromatic hydrocarbons
polycyclic aromatic hydrocarbons exists in
fullerenes and carbon nano tubes
in polycyclic aromatic hydrocarbons, you need to obey what rule and criteria for…
huckel’s rule
criteria for aromacity
what is the common sunscreen used
PABA
what is the common environmental pollutant
Benzo[a]pyrene
pesticides DDT is formed by what reaction
cholrination
sulfanilamide is formed by what reaction
nitration reaction
how many pi bonds do benzene have
6
in halogenation,
what is added to the benzene and in the presence of…
X2
FeX2 (lewis acid catalyst)
what is the product of halogentation
benzene attached to X + HX
in nitration,
what is added to the benzene and in the presence of…
HNO3 (nitric acid)
H2S04 (sulfuric acid)
in sulfonation,
what is added to the benzene and in the presence of…
H2SO4 (sulfuric acid)
heat
in alkylation (friedel-crafts),
what is added to the benzene and in the presence of…
RCl (alkyl halide)
AlCl3 (lewis acid catalyst)
in alkylation,
what is added to the benzene and in the presence of…
CH2=CH2 (ethene)
H+
in acylation (friedel-crafts),
what is added to the benzene and in the presence of…
acyl chloride (search up the structure)
AlCl3 (catalyst)
what is the product of nitration
nitrobenzene + H2O
what is the product of sulfonation
SO3H attached to benzene (benzenesulfonic acid) + H2O
what is the product of alkylation (friedel-crafts)
R(R is an alkyl group) attached to benzene (alkyl benzene) + HCl
what is the product of alkylation
ethylbenzene only
what is the product of acylation (friedel-crafts)
look at textbook
