Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Q1- Give the IUPAC name for each of the following compounds
H
C
CH2
Br
(ii)
(i)
Cl
OH
(iii)
Br
Br
Ph
NH2
Cl
(v)
(iv)
F
Br
C
Br
(vi)
CH
CH2-CH2-CH2OH
m-Xylene
(viii)
(x)
(vii)
(ix)
(i) 4-Bromo-1,2-dimethylbezene or 4-Bromoxyelen
(ii) Diphenylmethane
(iii) 1-Choloro-4-vinyl benzene or 4-Chlorostyrene
(iv) 4-Bromo-2-phenyl phenol
(v) 2-Bromo-1-chloro-4-flouro benzene
(vi) 2,5-Dibromo aniline or 2,5-dibromophenylamine
(vii) 1-Phenyl acetylene or ( Ethynyl benzene)
(viii) 1,3-Dimethylbenzene
(ix) 6-Benzyl-3-octene or (2-ethyl -4-heptenyl)benzene
(x) 4-Phenyl butanol
1
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Q2- Draw the structure of the following compounds
CH3
NH2
OH
O2N
NO2
NO2
m-Diisobutylbenzene
2,4,6-Trinitrotoluene
NH2
p-Aminophenol
p- Ethylaniline
Br
Cl
Benzyl bromide
o-Chlorostyrene
Br
m-Bromoisopropylbenzene
OH
Br
Cl
4-Bromo-2-chloro-1-ethylbenzene
4-Benzylhexyne
o-Xylene
CN
4-Allyl-3-cyanophenol
2
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Q3. Provide the product (s) of the following chemical reactions:
(CH3)2CHCl
O2N
O2N
AlCl3
O
O
Br2 / FeBr3
Br
O
O
Cl
+
AlCl3
O
NO2
NH2
NH2
HNO3 / H2SO4
NH2
+
O2N
COOH
KMnO4 / Heat
COOH
OC2H5
SO3 / H2SO4
+
SO3H
3
OC2H5
OC2H5
HO3S
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Br
Br2 / UV light
(Major product)
O2N
CH3
KMnO4 / Heat
Br
i)Mg / dry ether
ii) H2O / H
4
O2N
COOH
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Q4. Indicate whether the following structure is aromatic or not
aromatic? Give reason in each case.
CH3
Not aromatic
it has a sp3 carbon atom
Not aromatic because:
n=1.5
Aromatic because:
Not aromatic
cyclic, planar, each c-atomithas
haspaorbital
sp3
and n=1
carbon atom
Br
Not aromatic because:
n=1.5
Aromatic because:
cyclic, planar,
each c-atom has p orbital
and n=1
Not aromatic
it has a sp3 carbon atom
Not aromatic
it has two sp3 carbon atoms
Not aromatic because:
n=2.5
Aromatic because:
cyclic, planar, each c-atom has p orbital
and n=2
5
Aromatic because:
In each ring
cyclic, planar, each catom has p orbital and
n=1
Aromatic because:
cyclic, planar, each c-atom has p orbital
and n=1
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
Q5- Show how would you obtain the following compounds via
electrophilic aromatic substitution reaction(s)
HNO4 / H2SO4
O2N
COOH
COOH
SO3 / H2SO4
CH3
Br
Cl
HO3S
CH3
CH3
Br
/ AlCl3
O
CH3
CH3
O
CH3Cl / AlCl3
NO2
NO2
(CH3)2CHCH2CH2Cl / AlCl3
CH3Cl / AlCl3
H3CO
HOOC
H3CO
CH3
HOOC
CH3Cl / AlCl3
Cl
O
CH3CH2CH2CH2COCl / AlCl3
O
PhCOCl / AlCl3
6
Self Assessment Test- 5- Benzene and aromatic compounds
Dr. Nahed Nasser
6-Multiple choice questions:
(a) The electrophile in the acylation of toluene is
i) CH3Cl
ii) CH3
iii) CH3CO
iv) CH3COCl
(b) All bonds in benzene are
i) Polarized
ii) Localized
iii) Delocalized
iv) Ionic
(c) Length of bonds in benzene ring equals
i) 1.54 Ǻ
ii) 1.39 Ǻ
iii) 1.34 Ǻ
iv) 1.50 Ǻ
(d) Benzene is more stabilized than 1,3,5-cyclohexatriene by
i) 36 Kcal/mol
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ii) 85.8 kcal/mol
iii) 55.2 kcal/mol
iv) 28.6 kcal/mol