Part-02
Discussed Type in this Lecture
Type
Importance
Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
06
Substitution Reaction of Benzene and Toluene

Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
MCQ
Admission test years
BUET’ 12-13,
CKRUET’ 20-21,
KUET’ 18-19, 16-17, 13-14, 12-13,
11-12, 10-11,
RUET’ 12-13,
CUET’, 15-16, 14-15, 13-14, 12-13,
IUT’ 21-22, 20-21, 19-20, 14-15,
Written
BUET’ 20-21, 17-18, 12-13, 09-10, 05-06, 03-04,
01-02, 00-01,
RUET’ 10-11, 07-08, 04-05, 03-04,
CUET’ 09-10, 07-08, 03-04,
BUTEX’ 20-21
Importance

Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Reactions of Benzene:
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Reactions of Benzene:
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Reactions of Benzene:
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Toluene preparation:
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Toluene preparation:
Name of reaction
Wurtz-Fittig reaction
Friedel-Crafts alkylation
Reaction
Cl + 2Na + CH3 Cl
+CH3 Cl
𝐃𝐫𝐲 𝐞𝐭𝐡𝐞𝐫
Δ
𝐃𝐫𝐲 AlCl3
CH3 + 2NaCl
CH3 + HCl
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Reactions of Toluene:
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
 TNT:
Preparation:
+2HO − NO2
𝐜𝐨𝐧𝐜.
fuming 2HNO3
conc.H2 SO4 ,60C
30C
+ 2H2 O
𝐜𝐨𝐧𝐜.H2 SO4
+ 2H2 O
fuming 2HNO3
𝑐𝑜𝑛𝑐. H2 SO4 ,
110°C
❖ The explosion reaction is as follows:
Detonation
+2[O]
14 CO g + 3 N2 g + 5 H2 (g)
+ H2 O
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Which of the following reaction is incorrect?
(a)
(b)
Access dry AlC𝑙3
+CH3 I
+Br2 aq
100°C
25°C
[IUT’21-22]
+HI
+HBr aq
H
H
H
|
|
|
H2 O
(c) H3 C − C = O + CH3 MgBr → H3 C − C − OMgBr
H3 C − C − OH + Mg OH Br
|
|
CH3
CH3
(d)
+H − OH →
+Mg OH Cl
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ An explosive named Amatol is used to destroy old buildings. What is the Amatol
mixture composed of?
(a) Nitroglycerine and TNT
(b) Nitroglycerine and NH4 NO3
(c) TNT and NH4 NO3
(d) TNT and HNO3
(e) Nitroglycerine and DNT
[CKRUET’20-21]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❑ Which reaction is not possible?
[IUT’19-20]
(a)
(b)
(c)
(d)
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Which of the following is produced from Clemmensen reduction of benzaldehyde? [BUTEX'15-16]
(a) Benzene
(b) Benzoic
(c) Toluene
(d) Benzyl alcohol
❖ Which of the following compounds shows both aromatic and aliphatic properties?
(a) Chlorobenzene
(b) Toluene
(c) Cyclohexene
(d) Benzene
[CUET'15-16]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ What is the role of HNO3 in the reaction of
(a) Base
(b) Catalyst
+ HNO3
(c) Acid
Con.H2SO4
(d) Indicator
❖ What is produced when toluene is oxidized with strong oxidizing agent?
(a) Benzaldehyde
(b) Benzoic Acid
(c) Benzene
[CUET'15-16]
+ H2O?
60oC
[BUTEX’14-15]
(d) Benzo phenol
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Which one of the following functional groups is meta-ditecting?
(a) −NH2
(b) −OH
(c)−COOH
[BUTEX’14-15]
(d) −CH3
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Which one is Friedel Craft reaction?
(a) C6 H5 Cl + Mg
dry Ether
C6 H5 − MgCl
(c) C6 H6 + H2 SO4 100°C C6 H5 − HSO3
(e) C6 H6 + CH3 CH2 Cl
[KUET’13-14]
(b) C6 H5 Cl + NaOH + HCl → C6 H5 OH
(d) C6 H5 OH + PCl5 → C6 H5 Cl
dry aluminium chloride
C6 H5 CH2 − CH3
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ The major product of the following reaction would beBr2
FeBr3
?
(a)
(b)
(c)
(d) Equal amount of B and C
[BUET’12-13]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ What will be produced if toluene is oxidized by air & vanadium Penta oxide V2O5 at 500°C?
[KUET’12-13]
(a) benzoic acid
(b) benzene
(d) methyl benzoic acid
(e) ethyl benzene
(c) benzaldehyde
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ What is the percentage of hydrogen in TNT?
(a) 1.61%
(b) 2.17%
(d) 3.22%
(e) 2.81%
[KUET’11-12]
(c) 1.82%
❖ Which one is produced from the reaction between methyl chloride and toluene in
presence of anhydrous AlCl3 ?
[CUET’11-12]
(a) o − xylene
(b) p − xylene
(c) o − xylene and p − xylene
(d) None of these
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Complete the following reactions:
(i)
+2 Na + CH3 Cl
Dry ether
∆
[BUET'20-21]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ What is the difference in the mechanism of explosion between nitroglycerin and TNT?
Write the explosion reaction of TNT.
[BUET'20-21]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ How toluene can be converted into benzene and benzene can be converted into toluene?
Show by using chemical reactions.
[BUET'17-18]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Write the reactions for preparation of TNT from ethyne.
[BUTEX’20-21]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ (a) Acetophenone is reduced to ethyl benzene by refluxing with Zn Hg in a strongly
acidic medium. Mention the name of the reaction and show the reaction.
❖ Complete the following reactions
(i)
(ii)
(iii)
+Cl2
+Cl2
+Cl2
111o C
Light
111o C
Light
111o C
Light
[BUET’12-13]
[RUET’10-11]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Fill up the blanks of the following reactions.
(a) 2 +2CH3 I
(b)
(c)
(d)
(e)
dry AlCl3
+NaOH(CaO)
Δ
400o C
150 atm
+2H2 O
. . . . . . . . . . . . +Na2 CO3 (CaO)
dehydrate AlCl3
+CH3 COCl
+2NaOH
+. . . . . . . . . . . . . . +2HI
20°C
HCl
Δ
+−−−−− −
. . . . . . . . . . . . . . . . . +NaCl + H2 O
+. . . . . . . . . .
[RUET’07-08]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ How will you prepare alkyl aryl ketone with the help of benzene and acetic acid? What
is the name of the final reaction?
❖ Explain with example
(i) nitration (ii) acylation
[BUET’05-06]
[RUET’04-05]
Type-06: Aromatic Hydrocarbon: Benzene, Toluene, Orientation And Electrophilic
Substitution Reaction of Benzene and Toluene
❖ Write with equations what happens if ortho and para nitro toluene is heated with
fuming HNO3 and conc. H2 SO4 .
[CUET’03-04]
❖ Why meta-bromo toluene is not obtained directly by direct bromination of toluene or
by Friedel Crafts alienation of bromobenzene?
[BUET’01-02]