CHEMISTRY-12 147 UP-TO-DATE OUESTION BANK

CHAPTER-9 AROMATIC HYDROCARBONS

MULTIPLE CHOICE QUESTIONS (MCOs)
9.1 INTRODUCTION
1. Aromatic hydrocarbons are the derivatives of:
Ex.ii) (SDG-G2)-15, (SGD-G1)-17
(MTN-G1),(LHR-G1),(GUJ-G1)-19
Normal series of paraffins (B) Alkene
C) Benzene (D) Cyclohexane
Aromatic compounds burn with sooty flame
because: Ex.(ix) (RWP)16,(DGK-G1)-19
(A) They have high percentage of hydrogen
(B) They have a ring structure
(C) They have high percentage of carbon
(D) They resist reaction with air
2 NOMENCLATURE
No MCQ's has been taken from this topic.
3 BENZENE
The resonating contributing structures of
Benzene are: (LHR-G1)-16
(A) 2 (B) 3
The benzene molecule contains:
C5 (D) 7

Ex.i) (GUJ)-14,(BWP)-15
(MTN-G1)-16, (RWP-G2)-17,(DGK-G1)-18, (FBD-G1)-19
(A)three double bonds (B) two double bonds
(C)one double bond D) delocalized t -electron cloud

MODERN cONCEPTs ABOUT THE

9.3.5 STRUCTURE OFBENZENE ATOMIC ORBITAL
TREATMENT OF BENZENE
5. The structure of Benzene is: (MTN-G2)-16
Hexagonal irregular (B) Tetrahedral
(A) D Hexagonal planner
(C) Trigonal planner
9.3.6 THE STABILITY OF BENZENE
6. The carbon-carbon (C-C) bond length in benzene
is: (GUJ)-18
1.54 A
(A) 1.34 A (B) 1.20 A° (C)1.39 A° (D)
9.41 PREPARATION OF BENZENE
7
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 CHEMISTRY-12 148 UP-TO-DATE OUESTTON BANK CHEMISTRY-12 1439 UP-TO-DATE OUESTTION BANK
7. The conversion of n-hexane into benzene by (D) Nitration of m-chlorobenzene
heating in the presence of Pt is called: 15. Amongst the following, the
Ex.(x(BwWP)-15, (BWP-62)-17,(MTN-G2)-18 most readily compound that can be
sulphonated is:
(BWP-G2)-19
(B Aromatization
Ex.(v)
(MTN)-14,(SGD-G2)-15,(LHR-G1)-17
(A) Isomerization A Toluene (B) Benzene
(C)Dealkylation (D) Rearrangement (C) Nitro-benzene (D) Chloro-benzene
9.5 REACTIONS OF BENZENE 16. Which one is not a meta directing
group.
HNO+ Hso (DGK-G1)-15
8. Toluene 100C (LHR-G1)-14 (A)-COOH (B)-CHO (C)-COR (DNH
(A) Ortho-nitrotoluene (B) m-nitrotoluene 9.5.2 Electrophilic Substitution Reactions
(C) P-nitrotoluence D 2,4,6-TNT 17. Which of the following acid can be used as a
9. During Nitration of Benzene, the active nitrating
agent is: catalyst in Friedel Craft's reactions? (SWL)-15
(GUJ),(LHR),(FBD)-14,(DGK-G1)-15 (SWL),(AJK)-16, (RWP-G1),(MTN-G1)-17,(RWP)-18
Ex.(vi) (SGD-G1), (LHR-G1),(DGK-G2)-16
(GUJ-G1),(DGK-G1)-17,(DGK-G2)-18, (BWP-G1),(RWP)-19 AAICl (B) HNO (AJK),(SWL)-19
(C) BeCl (D) NaCI
(A) NO, NO (C) NO (D) HNO Orientation of Electrophilic
10. Which of the following is Ortho and 9.5.4
Para Substitution reactions
directinggroup? Wn).NOQBpk.com 18. Which one of the following species is an electron:
(SGD-G1)-14
(SGD-G1)-19
(A)-CHB) -CHO(C)-OH (D)NH
A -I (B) CHO (C) COOH(D)-NR
11. Benzene cannot undergo:(LHR-G2)-14,(MTN-G1)-15
9.6
COMPARISON OF REACTIVITIES OF
Ex.(iv) (RWP),(MTN-G2),(LHR-G2),(FBD)-17,(SWL)-18
(FBD-G2)-19 19.
ALKANES, ALKENES AND BENZENE
Which compound is the most reactive?
(A)Substitution Reactions (B) Addition Reactions (RWP)-14 (RWP),(LHR-G2)-15,(MTN-G2)-18,(SGD-G2)-19
(C)Oxidation Reactions (D) Elimination Reactions (A) Benzene
12. Which catalyst is used in Friedel Crafts Reactions. B)Ethene (C) Ethane (D) Ethyne
Ex.(ii) (SWL),(MTN),(DGK-G2)-14 SHORTOUESTIONS (SOs)
(SGD-G1)-15,(RWP-G1)-17,(FBD)-18,(MTN-G2)-19 9.1
1. What
INTRODUCTION
are monocyclic and polycyclic aromatic
AAICI, (B) BeC (C)NaC (D)HNO, hydrocarbons. (BWP)-14,(LHR-G1)-18,(SWL)-19
13. The electrophile in Aromatic sulphonation is: OR How Aromatic Hydrocarbons are classified?
Ex.(vii)(FBD),(GUJ),(BWP)-14,(GUJ-G2),(MTN-G2)- OR What are polycyclic aromatic hydro-carbons? Give
15(FBD),(AJK)-15,(SWL),(DGK-G2),(BWP-G1),(SGD-G2)-17 two examples.
(BWP-G1),(FBD), (SWL)-18,(DGK-G2),(GUJ-G2)-19 OR What are the two main classes of polycyclic

(A)H,SO (8)HSO aromatichydro-carbon? Give one example of

14.
Cso
m-chloronitro benzene is prepared by: (DGK)-14
(D) SO each.
OR What are aromatic hydrocarbons? Give two
(A) Nitration of chlorobenzene (LHR-G2),(FBD-G2)-14
B Nitration of Benzene examples:
(DGK-G1),(RWP-G2)-17,(BWP-G2)-18,,(LHR-G1)-19
(C) Chlorination of Nitrobenzene OR Draw the structures of
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CHEMISTRY-12 150 UP-TO DATE OUESTION BANR GHTMISTRYJ7 155 U210-DAT OU1STON PAN
(0) Naphthalene () Anthracene. (GU) G2) 15
(SGD G1)(DGN-G1)- 16(SGD-G1)-18,(DGK-G1),(SGD-G2) 19 4 Write structural formulas
Ans: a) Monocycdk Aromatic Hydrocarbons: diphenyl methane. bipheny and
and
(FB0)-17
Aromatk hydrocarbons containing one benzene ring in Ans
their moiecule are called mono-cyclic aromati a)
hydrocarbons
(4)
Bpheny Dighen menhare
5 Write down the structural formulas of
(a) Naphthalene (b) Phenanthlene
Ans: (a) Naphthalene: (SG0G1>19
Polycycdic Aromatic Hydrocarbons: (b) Phenanthene
Aromatc hydrocarbons containing two or more benzene
ring n their moiecules are called polycyclic aromatic
hydrocartbons They may be divided into
Those in which benzene nngs are isolated
()
CH 9.2
6.
NOMENCLATURE
Draw structural formulas
of p -nitrotoluene and
Dpheny methane
p Dibenzyl benzene. (GUJ-G1-19
Those in which benzene nngs are fused together at Ans: p nitrotoluene: P-Dibenzyi benzene
ortho position so that the adjacent rings have a common
carbon to carbon bond
( ()

Write down structural formulas of the followings

Write structural formulas of:
a) Naphthalene b) Diphenyl methane(LHR-G2)-17 (a) 3- Chloro iodo benzene
Ans: (b) 2 Bromo nitro benzene (BWP-G2-19
Ans: (a) 3-Chloro iodo (b) 2-8romo nitro
b)
CH benzene benzene

3 Write down the formula of Aniline and

Benzaldehyde. (SWL) 14
Ans:
()
9.3 BENZENE
8. How is benzene converted to nitro benzene and
bherca
toluene? (RWP-61)-17
Ans: i) Benzene to nitro benzene:

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CHEMISTRY-12 152 UP-TO-DATE OUESTTION BANK cHEMISTRY-12 153 UP-TO-DATE OUESTION BANK
11. How is the straight chain structure of benzene
ruled out?
H,SO (BWP-G2)-17
HONO H,O AnS: Two of the possible open chain structures
50 55C benzene are:
suggested for

ii) Benzene to Toluene:

I CliC1 C11 (1,5-Hexadiyne)
CH3 I I 1 (1,5-Hexadiene-3-yne)
AICl3
A Compound having structure as shown above should
CH,CI behave like alkene or alkyne, both are oxidised by
alkaline KMnO, oxidation.
Toluene
) Compounds ike these should give three types of
monosubstituted products.
9. How benzene is prepared from sodium benzoate
a)
and phenol? (RWP-G2)-17,(BWP-G1)-19
Ans: FromSodium benzoate:
COONa
b)
CaO
+NaOH
Na,CO,
C
BenzenE

From Phenol: but benzene gives oniy on mon0 substitutd oroduct.

OH The molecular formula fenzene C H 102s not
CorrespOd to any open char nydrOcarbur.
That is how straght chain structure of b2Ene ruled
ZnO
Out.
12. How will
you, prove that benzene has cyclic
eizee
structure? nODBPt.cm (LHR-G1)-17
10. What objections were raised on the Kekule's Ans: Benzene has cyciic structure as
structure for benzene molecule? i) Benzene gives oniy one mor0-substituted product
(DGK-G1)-16 X
(AJK),(SGD, 61)-16, (DGK-G2),(MTN-G1)-17,(DGK-G2)-18
Ans: Objections to Kekule's formula.
There are following objections raised on the Kekule's
structure for benzene molecule.
Kekule's formula with three double bonds demands a
high degree of unsaturation from benzene while usualy and gives three di-substit uted products.
it exhibit a saturated character.
i) Benzene vields substitution productsreadily and form
addition products reluctantly.
) Benzene is very stable compound. Y

9.3.2
Straight Chain Structures Ruled Out
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CHEMISTRY-12 154 UP-TO-DATE OUESTTON BANK CHEMISTRY-12 155UP-TO-DATTE
UESTION BANK
Further more X-ray studies prove the cyclic hexagonal OR Write down the Resonance structures
structure of benzene where all angles are of 120". All c. OR What is resonance. Draw two of Benzene.
OR
structure of benzene? resonances
C and C-H bond iengths are 1.397A and 1.09A OR Write down four Resonance structures of
Benzene. (LHR-G1)14, (SGD-G2), (MTN-G1)-16
respectively.
9.3.3 KEKULE'S STRUCTURE (RWP)-16,(MTN-G1),(SGD-G2)-17,(GU)-18,
Ans: Resonance Structures of
Benzene:
(SGD-G1)-19
13. What are the main points given by Kekule for The possibility of
different pairing schemes of valence
structure of benzene? (GUJ-G1),(FBD-G2)-18 electrons of atoms is called Resonance
and the different
Ans: In 1865,Kekule proposed à cyclic regular hexagonal structurees thus arranged are called
structure for beneze, which contains three double bonds structurees.
Resonance
alternatin9 with three single bonds. He prosed the Resonance is represented by a double headed arrow
structural formula as:
( ).
Different resonating structures of benzene are:

9.3.4 X-RAY STUDIES OF BENZENE STRUCTURE Kexule's structures Oewar str uCtures
17. Define Resonance Energy. Give Resonance energy
14. Describe
OR
Describe X-Rays
X-rays structure of Benzene.
studies of benzene structuure. of Benzene.
(BWP-61)-17, (RWP),(SWL)-19 OR How do you justify that 150.5 kJmolis the
Ans: X-Rays Studies of Benzene Structure: resonance energy of benzene?
The X-ray studies of benzene have confirmed the (GUJ)-14,(GUJ-G2),(LHR-G1)-15
hexagonal structure for it. These studies have also (MTN-G1),(SGD-G2),(RWP-G1)-17,(MTN-G1)-18
Ans: Resonance Energy:The difference between amount of
revealed that all the carbon and hydrogen atoms are in
heat actually released and that calculated on the basis of
the same plane. All the angles are of 120°. All C-C and Kekule's structures is called Resonance energy of the
C-H bond lengths are 1.397 A and 1.09A,respectively Compound.
It means benzene shows the phenomenon of Resonance
15. Write two objections that were raised on Kekule's
which makes it more stable than others.
structure for benzene molecule. (MTN-61)-19
Resonance energy of Benzene:
Ans: Objections:
(i) Kekule's formula with three double bonds demands a Calculated AH (3x -119.5) - -358.5k/mol
Observed AH 208kJ/mol
high degree of unsaturation from benzene while it = 150.5kJ/ mol
usually exhibity a saturated character. Difference
(i) Benzene yields substitution products readily and forms So,Resonance energy of Benzene is 150.5k3/mol
addition products reluctantly.
9.4 5PREPARATION OF BENZENE
9.3.7 THERESONANCE METHOD 18. heptane into toluene?
Convert
16. Describe the structure of Benzene on the basis of Ans: Heptane- Toluene
Resonance.
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CHEMISTRY-17 156 UP-TO-DATE OUESTION BANK CHEMISTRY-12 157 UP-TO-DATE QUESTION BANK
H
CH
CH

C,0, AlO, S0.

CH
CH
500c
4H
Cr,0, Al,0, S0 4H
500c
n Heptane Toluene
HC CH
19. What is Wurtz-Fitting reaction?(GUJ),(LHR-G2)-14 CH2 Toluene

(AJK),(RwP),(MTN-G1)-15, (MTN-G1)-16,(LHR-G1)-18 n-heptanhe

22. How is
benzene prepared from the
(DGK-G2),(AJK)-19 given
Ans: Wurtz-Fitting reactions: compounds? (a) n-Hexane (b) Sodium benzoate.
The Wurtz reaction for the synthesis of alkanes was (MTN-G2)-19
extended by Fitting in 1864 to the syntheses of Alkyl Ans: (a)n- Hexane
Aromatic Hydro-carbons.
CH CH

2Na +2NaBr
CH CH Br
Etner

20. Benzene can be prepared commercially from (b) Sodium benzoate:

acetylene. Give reaction with conditions. INoOH NaCO
(SWL)-14, (LHR-G1)-15,(GUJ-G1)-19
Ans: Preparation of Benzene from Acetylene: 9.5 REACTIONS OF BANZENE
23. What does happen to benzene during Friedel
3CH CH
Nu Ke Craft's reaction? Give mechanism of one reaction:
70 Ans: Friedel Crafts Reactions: (LHR-G2)-14,(AJK)-16
The alkylation and acylation of benzene are called
7
21. How Hexane and Heptane can give Benzene and Friedel Crafts reactions.
Toluene respectively? (MTN-G2)-15,(MTN-G1)-18 a)
a) Alkylation: The introduction of an alkyi group (-R) in
OR How will you distinguish chemically between the benzene ringing the presence of an alky! halide and
toluene and benzene. AICI, is called Friedel Craft's alkylation. e.g.
(DGK-G1),(SWL)-18
Ans: i) n-hexane Benzene
Benzene is an aromatic compound prepared from n AICI HX
R-X
haxane. Benz
Zene
Berizene

CrO Al0 SIO,

O

S006
b) Acylation: The introduction of Acyl group( R C)in the
benzene ring in the presence of an acyl halide and a
n-hexane Benzene
Toluene: catalyst AICI, is called Friedel Craft's Acylation. e.g.
ii) n-heptane
Toluen 5 an aromat.c tompound prepared from n
haptane

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 CHEMISTRY-12 158 UP-TO-DATE OUESTION BANK CHEMISTRY-12 159 UP-TO-DATE
JESTION BANK
O
AlCT,
CH The introduction of Acyl group(-C R) in the benzene
CH C CL HCI

ring in the presence of an acyl halide and

is called Friedel-Crafts
catalyst AICI
Acetophenone Acylation.
Mechanism (Acylation): Example:

R-CCI AICl, R C + AICI, CCH HC

AIO
H CH C

R R
Acetophenone
Mechanism:

C-R R C Cr AICI R C+AICI,

C-R AICI HCI AIC
H
O O
Acyl benzene R C-R
24. Write down mechanism for Halogenation of
benzene.(GUJ)-14,(GUJ-G2),(SwL)-18,(DGK-G1)-19
Ans: Halogenation of benzene:
-R
C C-R AICI + HCI AICI,
Cr H H

Acyl benzene
Mechanism: 26. How Acetophenone can be obtained from
X. FeX, X-FeX. benzene. (BWP)-144
Ans
CI -FeC, CI-FeCL
C CH
AIC
Cr H H CH CC HCI

Acetophenone

FeCl H HCI-FeC 27. Give the mechanism of Nitration of benzene.

(RWP)-14, (AJK),(LHR-G2),(LHR-G1)-16
25. How Acylation of Benzene takes place. Give its
(MTN-G2)-17,(RWP)-18
mechanism? (LHR-G1)-14 Ans: Nitration of Benzene: Introduction of (NO,) group in
Ans: Acylation of Benzene:
benzene ring is called "Nitration".

159
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 CHEMISTRY-12 160 UP-TO-DATE OUESTTION BAN CHEMISTRY-12 161 UP-TO-DATE OUESTION BANK
29. Give Reaction of Benzene with
SO,.(LHR-G2)-15
HONO H,O (BWP-G1)-19
Ans: Reaction of Benzene with
S0 55

SO,:
Mechanism: SOF
HS0,
HONO H.HS0. S0S5, NO: HSO H,O SO, 25C

Benzene Sulphoric cId

NO:
30. Prepare m-chloronitro benzene from benzene in
S0c
two steps.
NO
Slow Ex.Q.12(a)(SGD-G1),(BWP)-115
Ans: Benzene can
(DGK-G2)-18,(GUJ-G2),(AJK)-19
be converted into m-chloronitrobenzene
through the following 2-steps:
NO, NO
HSO
H.SO
Conc. HNO,
Cnc HSO4. A 2 anhvu. AJCT1. A
(Nitratwn) Chlonnauon
Nitro benzene C
Benzene Nurobrni*ne
28. Give two addition reactions of benzene. mchoronuo
benzene
OR Give two reactions to confirm the presence of
three double bonds in benzene. 31. How para-chloronitrobenzene is prepared from
OR Write two questions in which benzene is as benzene in two steps.
unsaturated compound. Ex.Q.12(b)(SGD-G2)-15,(BWP-G1)-19
(SWL)-16, (SGD-G1),(sGD-G1),(SWL)-17,(SGD-G1)-18 Ans: P-chloronitrobenzene canbeprepared from benzene by
Ans: Addition Reactions: the following 2-steps.
i) Reduction: Step ()
N at 200co
3H
+a FeCl
Ol +HO

Cydohexane Step (ii)

ii) Halogenation
NO

3Br
Sunight 2 2(HNOH04) 2H,O

0- Chlor0 NO
nitrobenzene
p - Chloronitrobenzene

1, 2,3,4, 5,
6-Hexabromo be nz ene

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CHEMISTRY-12 162 UP-To-DATE OUESTION BANK CHEMISTIRY-12 163 UP-TO-DATE QUESTION BANK
How will you prepare
2,4,6-trinitrotoluene from
32. CH
(GUJ)-17,(SGD-G2)-19 CH
benzene in two steps. NO
Ans: 1 step (Alkylation): HONO, S0
CH3
0-nitrotoluene
AIC
CH,CI
9.5.2 Electrophilic Substitution Reactions
Toluene 36.
36. Write down mechanism of Alkylation of Benzene.
Ans: Alkylation of Benzene: (SWL)-16
2nd step (Nitration):
CH CH3 R-C+AICT, >ACI, +R
ON NO2 R
HSO
HONO,
R
NO2
R R
246-Trinitrotoluene
H
33. What happens when benzene is oxidised AICI +HCI+ AiCI
withozone?
.on
(GUJ)-17 e.g.
Ans: Benzene reacts with ozone and gives glyoxal through CH
benzene triozonide.

CHO +CH CI Ha

30 CeHOg 3 CHO oluen

when benzene is heated with conc. 37. What happens when chlorine is passed through
34. What happens Benzene is sunlight?
HSO at 80°C? (MTN-G2)-17
Ans: When benzene is heated with conc.H,SO4at 80'C, Ex.Q.5(b) (MTN-G2)-16,(LHR-G1)-19
Ans: When chlorine is passed through benzene in the
benzene sulphonic acid is produced. presence of sunlight benzyl chloride is formed.
SOgH CH CH2CI
HSO, 80C
HO +Cl 2
sunlight
HCI

35. How will you prepare O-nitro toluene from

benzene in two steps?(DGK-G1)-17,(GUJ-G1)-18 Benzyl chlonde

Ans: CHC CHCI2

CH3

+CH,CI AICI3
sunlight
+Cl2 HCI

Benzal chloride

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CHEMISTRY-12 164 UP-TO-DATE OUESTION BANR CHEMISTIRY-12 165 UP-TO-DATE OUESTION BANK
CHCI
CCI
OR Give catalytic oxidation of benzene.
OR Reaction of Benzene with Ozone
OR
sullht OR
OR What happens when Ozone is reacted with
HCI Benzene?
C
OR
OR What happens when a mixture of benzene vapors
Benzotruchlonde
and air are passed over heated vanadium
and
nOBPk. Com
to chlorobenzene and pentaoxide? uwwRJ.
38. How is benzene converted Ex.Q.5(c) (MTN-61),(LHR-G1,2),(DGK-G2)-16
acetophenone? (BWP-G2)-17
>Chlorobenzene
(DGK-G1)(LHR-G2),(FBD),(SWL)-17,(FBD),(MTN-G2)-18
Benzene Ans: Ozonolysis:
Ans CI CHO
feCl
Cl2 HCI 30 C.HO 3I
CHO
Benzene >Acetoplhenone Benzene Benzene triozonidee Glyx
O. CH3 Catalytic Oxidation:
c
C
AICI
H,C-C-CI +HCI 90, 4CO 4hO
450C

39. What is the general pattern of reactivity of Benzene

benzene towards electrophiles? (LHR-G1)-17 Maleic anhydride
Ans: The highly stable delocalized electrons of benzene ring
are not readily available for the electrophilic attack by CH H COOH

weak electrophiles like the electrons of alkenes. It H,O-

CH HC COOH
means more powerful electrophiles are required to
penetrate and break the continuous sheath of electron O Maieic acid

cloud of benzene. The general pattern of reactivity of Maleic anhydride

benzene towards electrophiles can be shown as 41. What happens when acidified KMnO, is added to
E methyl benzene and ethyl benzene?(BWP-G1)-17 benzene
Ans: When acidified KMnO is added to methyl or

oxidised to benzoic acid.

ethyl benzene, they are
COOH
CH3
E
E
KMnOH
HB BH

9.5.3 Reactions of Benzene COOH

Ring CH,CH3
40. Explain the term Oxidation with one example
KMnO H
using benzene.
OR How benzene is converted into maleic acid by
catalytic oxidation? Reaction
Orientation in ElectrophilicSubstitution
164
9.5.4 165
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 CHEMISTRY-12 166 UP-TO-DATE OUESTTON BANK CHEMISTRY-12 167 UP-TO-DATE OUESTION BANK
of any four ortho-para directing
42. Write
groups?
name
(DGK-G1)-16 LONG OUESTIONS (LO
Ans: Ortho Para directing groups
are given below:
() OCH
9.1
What are
INTRODUCTION
Aromatic
() NH (1) -OH 1. Hydrocarbons? How are they
Br (vi)-I classified
(Iv C (v) ortho and para
(RWP)-15,(FBD-G2)-19
is
hydroxyl group(-OH)
43. Why
directing group?
(FBD)-16 9.2 NOMENCLATURE
Draw structural formula for the foilowing
ortho and para directing 2. compounds
Ans: Hydroxyl group (-O) IS
n chlorobenzoic acid i) 2,4,6- Trinitrotoluene
groupbeause the OH group
is strongly activating
a i)
aromatic directing groups). The -OOH ii) P Dibenzylbenzene iv) D Nitr0 aniline
group (Electrophilic
group tends to be electron-donating
because the extra (MTN-G2)-19
be shared with 3. Draw structural formulas of
following compounds
electrons around the oxygen atom can

the aromatic benzene ring. (i) m-Chorobenzoic Acid (1) 2,4,6trinitrotoluene

(ii) p-hydroxybenzoiC Acid (iv) m-Nitrophenoi
44 Definemeta-directing groups. (MTN-G1)-16
Ans: Meta-Directing Groups: Thegroup which hinde 2nrosp cm (GUJ-G1)-19
known
further substitution in the benzene nucleus are as 9.3 BENZENE
meta-directing groups. These groups with draw 4. Explain the structure of Benzene on the basis of atom c
electrons from the benzene ring there by reducing their orbital treatment. (LHR-G1),(BWP)-14,(MTN-G1)-15
availability to the electrophilees. (DGK-G1),(LHR-G1),(RWP-G1,2)-17. (DGK-G2)-3
45 How will you prepare m-chloronitro benzene form (BWP-G2).(RWP),(AK)-19
benzene in two steps? (MTN-G1)-19
Ans: Step 1:
5. Describ the structure of Benzene on the basis of
Resonance method (RWP)-14
6. Straight chain structure of Benzene is ruled out, Expian
(SGD-G1)-15
HNO H 7. Discuss xtra ordinary stability of Benzene moiecuies
OR Discuss the stability of benzene in detail with reference
Step 2: to 1, 3, 5-cyciohexatriene.
(SGD-G2)-15,(MTN-G2)-17,(MTN-G1)-18,(SGD-G1)-19
8. What is resonance? Explain the structure of benzene on
HC the basis of resonance. (GUJ)-17
9 Discuss how x-rays studies confirmed hexagonai
structure for benzene. Also discuss objections to
COMPARISON OF REACTIVITIES OF
9.6 Kekule's structure. (SWL)-19
ALKANES, ALKENES AND BENZENE 9.4
46.
OR
Benzen isless reattive than Alkene, why?
Justifythat ethene is more reactive than 10.
PREPARATION OF BENZENE
Discuss two Industrial and two laboratory methods to
benzene. (RWP),(FBD)-16,(SGD-G1)-17,(DGK-G1)-18 prepare Benzene.(GUJ)-14, (GUJ-G2)-15, (AJK)-16
Ans: Ethene is reactive due to inherent weakness of the OR Write down four methods for preparation of Benzene.
Dond and availability of the 7 -electrons for the (GUJ)-14, (MTN-G2), (LHR-G2)-16, (BWP-61)-17
11. Write the mechanism of Nitration and Alkylation of
electrophilic reagents vwhile benzene is a stable molecule
Gue to the delocalization of the lectronic cloud. Benzene.(SWL)-14,(RWP)-15,(FBD)-16,(SGD-G1)-17
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12. What are Friedel-Crafts Reactions? Explain mechanism 22. How does phenol reach with the
of alkylation and Acylation of Benzene.
folilowing reagents.
HNO i) NaOH
OR Write mechanism of FriedelCraft alkylation ànd acylation i)
(LHR-G1)-14,(LHR-G1),(DGK-G2)-15 ii) Zn v) Bromine water (DGK-G1)-15
(DGK-G1),(MTN-G1),(SGD-G1),(SWL)-16,(LHR-G2)-18
13. What happens when toluene is treatedwith?
23. Predict the major products of bromination of following
compounds along with reaction conditions
) i n the presence of sunlight. Nitrobenzene
i) i) Benzaldehyde
) KMnO, in the presence of HSO (LHR-G2)-14 i) Bromobenzene v) Phenol (RWP)-16
14. Write the mechanism of Halogenation of benzene. 24. How benzene reacts with:
(FBD-G2)-14 (i) Br in presence of sunlight)(ii) H
H
15 Give mechanism with an example of Friedel Crafts ii) Cl, (in presence of FeCl.)
Acylation Reactions. (DGK-G1)-14 (iv) CH, CI (in presence of AlCI,)
(Iv) (DGK-G2)-19
16. Wnte a note on Friedel Crafts Alkylation, give the
mechanism. (DGK-G2),.(MTN-G2)-14,(GUJ-G1)-18 Orientation of Electrophilic
9.5.4
17. i) Write mechanism of acylation of benzene
Wrte IUPAC names of the following:
Substitution reactions
25. Predict the major products of bromination of
CHO OH
i) Toluene i) Nitrobenzene
HC CH3 B zolapt can
ii) Bromo-benzene iv) Benzoic acid (SGD-G2)-17

Br CI
18. Describe nitration and sulphonation of benzene with
mechanism. (MTN-G1)-17
OR What is nitration of benzene? Give mechanism of
reaction. (LHR-G2)-17
OR Write mechanism of sulphonation of Benzene.
(LHR-G2)-14,(MTN-G2)-15, (FBD)-16
(LHR-G2)-17,(DGK-G1)-19
9.5
19.
REACTIONS OF BENZENE
Convert Benzene into:
(SGD-G61),(LHR-G2)-15,(RWP)-18,(BWP-G1)-19
Cyclohexane ) Maleic acid
) Glyoxal v) Benzene sulphonic acid
20. Write down two addition and two substitution reactions
of Benezene (GUJ-G2)-15
21. Detail out two reactions in which Benzene behaves as
saturated Hydrocarbon and two reactions in which it
behaves as unsaturated. (AJK)-15,(GUJ-G2)-19
169
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