AROMATICITY & HYDROCARBONS

AROMATICITY &
HYDROCARBONS
DPP - 01
Class : 11th - 2021
O
IDENTIFY AROMATIC ANTI-AROMATIC & 22. 23. 24.
NON-AROMATIC
SPECIES FROM THE FOLLOWING
O O
NC CN NH2
1. 2. 3.
N
Ph Ph
25. O 26. 27. N O
pyran H
cytosine
H3C CH3 N-
N+
4. 5. 6.
O
Dimethyl fulvene Calicene
28. 29. 30.

H
N
7. 8. 9.
CH2 Tropylium ion Pyrole 31. 32. 33.

H
O S N O
10. 11. 12.
Furan Thiphene N
Imidazole 34. 35. 36.
O
-pyrone

N
+
13. N 14. O 15. N O
Pyridine Pyrilium ion Pyrimidine

37. 38. N O 39. N

N
H H
O H
O
OH
16. N 17. 18.
Q u in o lin e
Tropone H
Tropolone N
+

40. N 41. 42.

O N
H pyrylium ion
+
19. +
20. 21.
O O
O
43. 44. 45.

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AROMATICITY & HYDROCARBONS

10. Friedel–Crafts' reaction does not occur in case of –

(A) Toluene (B) Benzene
+ (C) Naphthalene (D) Pyridine
46. 47. N 48. N
H 11. C6H6 + A  AlCl
1,2-dihydropyridine H  3
 C6H 5CONH2
A in the above reaction is –
(A) NH2CONH2 (B) CICONH2
(C) CH3CONH2 (D) CH2(Cl)CONH2
H 12. Benzene does not react with the following except –
B (A) Bromine in carbon tetrachloride solution
49. 50. 51. (B) Aqueous potassium permanganate solution
(C) Hydrogen in the presence of finely divided nickel at
high temperature and high pressure
(D) Dilute sulphuric acid in ethanolic solution
13. In nitration, H2SO4 is used as –
(A) Solvent
N N S
52. N 53. 54. (B) Dehydrating agent
O
isoxazole 1,3-thiazole (C) Sulphonating agent
H
(D) Nitronium ion producer
14. Which of the following compounds reacts slower than
benzene in electrophilic bromination -
(A) C6H 5 – NO2 (B) C6H 5 – NH2
HYDROCARBON EXAMPLE (C) C6H5 – OH (D) C6H 5 – CH3
01. The general formula of arenes is - 15. Which of the following is a polynuclear hydrocarbon -
(A) Cn H2n (B) CnH 2n–6 (A) Cumene (B) Naphthalene
(C) CnH 2n–4 (D) CnH 2n+2 (C) Mesitylene (D) Diphenyl
02. Pyrogallol is ......... trihydroxy benzene – 16. An arene containing three primary, three secondary and
(A) 1, 2, 4 (B) 1, 2, 3 three tertiary carbon atoms is –
(C) 1, 3, 5 (D) None (A) Cumene (B) Cymene
03. Which of the following statements is incorrect for (C) Mesitylene (D) Styrene
benzene – 17. Which of the following reactions of benzene does
(A) It is insoluble in water not prove the presence of three carbon — carbon double
bonds in it –
(B) It has tetrahedral structure
(A) Formation of a triozonide
(C) It freezes at 5.5ºC
(B) Hydrogenation of benzene to cyclohexane
(D) It floats in water
(C) Formation of C6H6Cl6 by addition of chlorine
04. Among the following groups, the group that deactivates
(D) Formation of nitrobenzene on heating benzene with a
the benzene ring for further electrophilic substitution, is mixture of concentrated nitric acid and sulphuric acid
(A) Hydroxyl (B) Methyl 18. The number of benzylic hydrogens in ethylbenzene is –
(C) Chloro (D) Amino (A) 3 (B) 5 (C) 2 (D) 7
05. The intermediate formed in the reaction of benzene with 19. Benzene does not undergo addition reactions easily
an electrophile is – because -
(A) Wheland intermediate (A) It has a cyclic structure
(B) – complex (B) Double bonds in it are very strong
(C) Benzenium cation (C) Resonance stabilized system is to be preserved
(D) All the above (D) It has six hydrogen atoms
06. Benzene reacts with benzoyl chloride to form - 20. The reaction of replacement of a hydrogen atom in
benzene by alkyl group can be brought about with the
(A) Benzophenone (B) Acetophenone
following reagents except –
(C) Benzylchloride (D) Maleic anhydride
(A) Alkyl chloride and AlCl3 (B) Alkene and AlCl3
07. Among the following statements on the nitration of aromatic (C) Alkanol and alkali (D) Alkanol and acid
compounds, the false one is –
21. Select the correct statement about benzene–
(A) The rate of nitration of benzene is almost the same
(A) Benzene possesses two types of carbon-carbon bonds
as that of hexadeuterobenzene
(B) Benzene usually undergoes addition reactions
(B) The rate of nitration of toluene is greater than that of
benzene (C) Benzene produces three monosubstitution products
(C) The rate of nitration of benzene is greater than that (D) Benzene involves cyclic delocalization of six -electrons
of hexadeuterobenzene 22. The dipole moment of chlorobenzene is 1.6 D. The
(D) Nitration is an electrophilic substitution reaction expected dipole moment of p-dichlorobenzene is -
08. Reaction of SO3 is easier in – (A) 1.6 D (B) 3.2 D (C) 1.62D (D) 0.0 D
(A) Benzene (B) Toluene 23. The following three isomeric tribromobenzenes are subjected
(C) Nitrobenzene (D) All the above to mononitration :
09. Carbocations are formed by all of the following reactions Br
except – Br Br
Br
(A) Addition of acid in an alkanol Br
(B) Abstraction of a hologen from an alkyl halide by
Lewis acid Br Br Br
Br
(C) Pyrolysis of alkanes I II III
(D) Addition of a mineral acid to an alkene Which of these would produce three possible
mononitrobromobenzenes ?
(A) II and III (B) I and II

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AROMATICITY & HYDROCARBONS

(C) II (D) III c) X = 1-butene, Y = 1-butanol

24. In the reaction, Cl2 + CH4  hv
 CH3Cl + HCl d) X = 1-hexane, Y = 1-hexanol
presence of a small amount of oxygen 32. An unsaturated hydrocarbon was treated with ozone
a) Increases the rate of reaction for a brief period of and resulting ozonide on hydrolysis gives 2-pentanone
time and acetaldehyde. What is the structure of alkene ?
b) Decreases the rate of reaction for a brief period of a) C3H7 - CH = CH - CH3
time C3H7 H
c) Does not affect the rate of reaction C=C
b)
d) Completely stops the reaction CH3 CH3
25. Chlorination of methane does not occur in dark
because CH3 C2H5
a) methane can form free radicals in presence of c) C=C
CH3 CH3
sunlight only
b) to get chlorine free radicals from Cl2 molecules
C3H7 CH3
energy is required. It cannot happen in dark
d) C=C
c) substitution reaction can take place only in sunlight CH3 CH3
and not in dark
d) Termination step cannot take place in dark. It 33. How many structures are possible for C5H8 with one
requires sunlight triple bond ?
26. Which of the following isomeric heptanes can yield a) 4 b) 3 c) 2 d) 1
seven different monochlorinated products upon free 34. Ozonolysis products of 2-pentyne after decomposition
radical chlorination ? of ozonide with water and subsequent oxidation are
a) 2,2-Dimethylpentane b) 2-Methylhexane a) ethanoic acid and propanoic acid
c) 3-Methylhexane d) 2,4-Dimethylpentane b) ethanoic acid and propanone
27. In the given reactions : c) ethanoic acid
Na,ether Br2 Na,ether
d) formic acid and glyoxal
i) CH3Br  X 
h
 Y  Z 35. Benzene easily shows
NaOH NaOH Br2 a) ring fission reactions since it is unstable
ii) CH3COOH   X 
CaO
 Y 
h
Z
b) addition reactions since it is unsaturated
Idenfity X, Y and Z c) electrophilic substitution reactions due to stable ring
and high  electron density
a) i) CH4 CH3Br CH3CH3 d) nucleophilic substitution reactions due to stable ring
ii) CH3COONa CH3CH3 CH3CH2Br and minimum electron density
b) i) CH3CH3 CH4 CH3Br 36. Which of the following steps is not correct in the
ii) CH3COONa CH4 CH3CH2CH3 mechanism of electrophilic substitution of benzene ?
c) i) CH3CH2Br CH3CH3 CH3CH2CH3 a) Generation of electrophile like X+, R+, RC+O, NO+2,
ii) CH3COONa CH4 CH3Br etc.
d) i) CH3CH3 CH3CH2Br CH3CH2CH2CH3 b) Attack of electrophile resulting in the formation of
ii) CH3COONa CH4 CH3Br arenium ion in which one of the carbon is sp3
28. How many geometrical isomers are possible for the hybridised
given compound ? c) Addition of proton on benzene ring to give
CH3 - CH = CH - CH = CH - C2H5 carbocation
a) Four b) Three c) Two d) Five d) Removal of proton from sp3 carbon atom to restore
29. Arrange the following alkyl halides in decreasing order aromatic character
of the rate of -elimination reaction with alcoholic
KOH 37. Arrange the following alkenes
CH3 - CH - CH2Br CH3 CH3
I. CH3CH2CH2Br II. C = CH2 II. C = CH2
CH3 I.
CH3OCH2 CH3
CH3 - CH2 - CH - CH3
III. CH3
Br III. C = CH2
a) ii > iii > i b) iii > ii > i c) i > ii > iii d) ii > i > iii CH3O
conc.H2SO4 Cl2 In decreasing order of their reactivity towards HBr
30. CH3CH2CH2OH 
170o C
A 
500o C
 B.
a) I > II > III b) II > III > I
A and B are c) III > II > I d) III > I > II
a) A = CH3CH2CH3, B = CH3CH2CH2Cl 38. Consider the following compounds :
b) A = CH3CH = CH2, B = CH2ClCH = CH2
c) A = CH2 = CH2, B = CH3CH2Cl I. II. III.
d) A = CH3CH2CH3, B = CH3CH = CH2
31. An alkene X is obtained by dehydration of an alcohol Which compound possesses highest dipole moment :
Y. X on ozonolysis gives two molecules of ethanal for a) I b) II c) Both I and II d) III
every molecule of alkene. X and Y are
a) X = 3-hexene, Y = 3-hexanol
b) X = 2-butene, Y = 2-butanol
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39. Arrange the following alkyl halides in decreasing order 46. Compound 'A' on chlorination gives compound 'B'
of the rate of -elimination reaction with alcoholic
KOH compound 'B' reacts with alc. KOH gives gas 'C', which
decolourise Baeyer reagent. ozonolysis of compound 'C'
H
gives only HCHO compound. 'A' is:
CH3 - C - CH2Br
I. II) CH3 - CH2 - Br
a) C2H6 b) C2H4 c) C4H10 d) C2H5Cl
CH3
47. An organic compound A(C4H9Cl) on reaction with
III. CH3 - CH2 - CH2 - Br
Na/diethyl ether gives a hydrocarbon which on
a) I > II > III b) III > II > I
c) II > III > I d) I > III > II monochlorination gives only one chloro derivative
then, A is
40. What is the major product of the following reaction ? a) t–butyl chloride b) Sec. butyl chloride
C6H6 + (CH3)2C = CH2  H3PO 4
? c) Iso butyl chloride d) n–butyl chloride
48. The compound CH3 C CH CH3 on reaction with
a) b) CH3

NaIO4 in the presence of KMnO4 gives:

a) CH3COCH3
c) d) Both (b) and (c) b) CH3COCH3 + CH3COOH
41. Ethyl benzene on heating with Cl2 gives A (C8H9Cl). c) CH3COCH3 + CH3CHO
A on reaction with alcoholic KOH gives B (C8H8) d) CH3CHO + CO 2
Compounds A and B are, respectively 49. The major product obtained on treatment
a) C6H5 - CH2CH2Cl and C6H5 - CH2 - CH2 - OH of CH3CH2CH(F)CH3 with CH3O /CH3OH is
–

Cl OH a) CH3CH2CH(OCH3)CH3 b) CH3CH CHCH3

b) C6H5 - CH - CH3 and C6H5 - CH - CH3 c) CH3CH2CH CH2 d) CH3CH2CH2CH2OCH3
c) C6H5 - CH2CH2Cl and C6H5 - CH = CH2
50. 2-Bromopentane is heated with potassium ethoxide in
Cl
ethanol. The major product obtained is -
d) C6H5 - CH - CH3 and C6H5 - CH = CH2
a) 1-Pentene b) cis-2-pentene
42. What is the correct increasing order of reactivity of the c) trans-2-pentene d) 2-Ethoxypentane
following compounds towards electrophilic aromatic 51. Monochlorination of ethylbenzene (PhCH2CH3) with
substitution reaction ?
Cl2 under heat produces -
CH3 a) PhCH2CH2Cl
CH3
b) PhCHClCH3
I. II. c) both (1) and (2) in equal amounts
CH3 CH3 d) more of (2) and less of (1)
52. Raney nickel, which is used as a catalyst, is
F CHO
III. IV. obtained by-
a) grinding solid nickel
a) I < II < III < IV b) IV < III < II < I b) by treating nickel–aluminium alloy with dilute NaOH
c) IV < III < I < II d) III < IV < I < II
c) by treating nickel–aluminium alloy with dilute HCl
43. In the formation of alkene when alcoholic KOH reacts d) by heating nickel tetracarbonyl
with CH3CH2Cl what is the attacking species in the 53. The major product formed in the dehydration of 1–
reaction.
butanol by heating with concentrated H2SO4 is -

a) C2H5O - b) OH- c) H 3 O
d) K  a) trans–2–butene b) cis–2–butene
44. What is the weight of bromine needed for the reaction c) 1–butene d) 1, 3–butadiene
with 21 gm of C3H6
(atomic weight of Br 80) 54. For the reaction
a) 40 g b) 80 g c) 160 g d) 120 g H2SO4
CH2OH
45. Lewisite a war gas is obtained by the action of
acetylene on the major product is
a) COCl2 b) SOCl2 c) AsCl3 d) AlCl3
a) CH2 b) CH3 c) d)

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55. Propene on reaction with ICl produces mainly - OH

|
a) 1–chloro–2–iodopropene O=C–CH2CH3 HC=C–CH3
b) 2–chloro–1–iodopropane
c) d)
c) (±)–2–chloro–1–iodopropane
d) (±)–1–chloro–2–iodopropane
AlCl3 -HCl
56. Which of the following will give the best yield of 2– 63. 
298K
 A, A is
pentene on reaction with C2H5ONa/C2H5OH
a) 2–Iodopentane b) 2–Bromopentane a) b) c) d)
c) 3–Iodopentane d) All equally satisfactorily
57. The bond dissociation energies of the following 64. Out of the following, which structures represent the
same compound ?
CH3–H CH3CH2–H CH2=CH–CH2–H C6H5–H
I II III IV
vary in the order
a) I > II > III > IV b) IV > III > II > I (X) (Y) (Z)
c) IV > I > II > III d) II > I > IV > III
58. Which is the decreasing order of strength of bases
a) X, Z b) X, Y c) Y, Z d) X, Y, Z
OH–, NH 2 , HC  C– and CH3– CH 2 Cl2
65. 
H 2O
 A, A is
a) CH3– CH 2 > NH 2 > HC  C– > OH–
Cl OH
OH Cl OH
b) HC  C– > CH3– CH 2 > NH 2 > OH– a) b) c) d) Cl
OH Cl

c) OH– > NH 2 > HC  C– > CH3– CH 2 66. CCl3CH = CH2 

Cl 2 + H 2O
 A, A is
CCl3CHCH2Cl CCl3CHCH2OH
d) NH 2 > HC  C– > OH– > CH3– CH 2 a) OH
b)
Cl
59. The chief reaction product of reaction between CCl3CHCH2 CCl3CHCH2
n-butane and bromine at 130º C is -[IIT-95] c) d)
Cl Cl OH OH
67. Most stable intermediate of the hydration of isopentene
a) CH3CH2CH2CH2Br b) CH3CH2CHBr
CH3CHCH = CH2 is
CH3
CH3

c) CH3–CHCH2Br d) CH3–C–Br2 CH3

CH3 CH3 a)) CH3CHCHCH3

60. CH3–CH=CH2  CH3

NOCl
 Product, product is :
b) CH3CCH2CH3
a) CH3–CH–CH2–NO b) CH3–CH–CH2–Cl
c) Both (a) & (b) correct
Cl NO
d) None of the above is correct
c) CH3–CH2–CH2–Cl d) NO–CH2–CH2–CH2–Cl 68. Examine the following two structures for the anilinium
ion and choose the correct statement from the ones
61. One mole of a symmetrical alkene on ozonolysis gives
given below :
two moles of an aldehyde having a molecular mass
+
of 44 u. The alkene is :- NH3 NH3
a) ethene b) propene c) 1-butene d) 2-butene +
I 
 II
CCCH3
62. In the given reaction  2 a) II is not an acceptable canonical structure because
H / Hg
  A the carbonium ions are less stable than ammonium ions
b) II is not an acceptable canonical structure because it
product 'A' is :- is non-aromatic
c) II is not acceptable canonical structure because the
O nitrogen has 10 valence electrons
||
HO–C=CHCH 3 d) II is an acceptable canonical structure
CH2–C–CH 3
69. p-Nitrotoluene on further nitration gives
a) b) a) 3,4-dinitrotoluene
b) 2,4-dinitrotoluene
c) 2,4-dinitrobenzyl alcohol
d) 2,5-dinitrotoluene

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AROMATICITY & HYDROCARBONS

70. Which of the following resonance structures contributes 77. Assertion : Boiling point of pentane is higher than
the most to the resonance hybrid ? 2,2-dimethylpropane
OCH3
Reason : There is steady increase in boiling point with
OCH3 OCH3 OCH3
increase in molecular mass
a) b) c) d)
+ 78. Assertion : Iodination of alkanes is carried out in the
presence of oxidising agents like HIO3 or HNO3.
71. Which of the following is not true about directing groups
in electrophilic aromatic substitution ?
Reason : Iodination of alkanes is an irreversible
a) Meta-directors deactivate the ring making the reaction
compound less reactive than benzene 79. Assertion : Staggered conformation of ethane is most
b) Activating groups are ortho, para-directors stable while eclipsed conformation is least stable.
c) For substituted compounds, the incoming electrophile Reason : Staggered form has the least torsional strain
determine the location of attack on the benzene ring and the eclipsed form has the maximum torsinal strain
d) For substituted compounds, the substitutent on the 80. Assertion : cis-form of alkene is found to be more
ring determines where the incoming electrophile attacks polar than the trans-form
72. Why halogens are deactivating yet ortho/para directing Reason : Since the groups are in opposite directions
in electrophilic aromatic substitution. in the trans-form, the dipole moments of bonds cancel
a) resonance electron release with no inductive effect
each other making trans-form almost non-polar
at all
b) a combination of inductive electron release and
81. Assertion : Addition of HBr to propene yields
resonance electron release 2-bromopropane but in presence of a peroxide it
c) inductive electron withdrawal with no resonance yields 1-bromopropane
effect at all Reason : When reaction is carried out in the presence
d) a combination of inductive electron withdrawal and of a peroxide it follows free radical mechanism, 2o free
resonance electron release radical is more stable than 1o free radical
73. Which of the following is most stable sigma complex 82. Assertion : Ethyne reacts with sodium metal and
formed when toluene undergoes para nitration ? sodamide to form sodium acetylide with the liberation
CH3 CH3 CH3 of dihydrogen gas
CH3
Reason : Alkynes are highly unsaturated
83. Assertion : In case of aryl halides, halogens are
a) b) c) d) moderately deactivating
H NO2 H NO2 H NO2 H NO2 Reason : Halogens are ortho, para directing groups
84. Predict major product of the following reaction
74. An organic compound C6H12(X) on reduction gives Conc.HNO3 Br2
C6H14 (Y). X on ozonolysis gives two aldehydes CH2 
Conc.H 2SO 4
? 
FeBr3
?
C2H4O (I) and C4H8O (II). Identify the compounds
X, Y and aldehydes (I) and (II) 85. Predict major product of the following reaction.
75. Name the products of the following reactions
I) C6H6 reacts with methyl chloride in presence of O
Br2
AlCl3 C - NH 
FeBr3

II) C6H6 reacts with acetyl chloride in presence of
AlCl3 86. Identify A to C in the following sequence of reactions :
III) C6H6 reacts with fuming nitric acid in presence of
conc. H2SO4 + CH3CH2CH2Cl 
AlCl3 NBS
 A  B
IV) C6H6 is catalytically hydrogenated
76. Assertion : Sodium salt of butanoic acid on heating AlC.KOH
 C
with soda lime gives butane
Reason : Decarboxylation reaction yields alkanes
having same number of carbon atoms as the parent
acid

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AROMATICITY & HYDROCARBONS

TOPIC : AROMATICITY & HYDROCARBOND

ANSWER-KEY
1 2 3 4 5 6 7 8 9 10 11
B B B C D A C B C D B
12 13 14 15 16 17 18 19 20 21 22
C D A B C D C C C D D
23 24 25 26 27 28 29 30 31 32 33
C B B C D A B B B B B
34 35 36 37 38 39 40 41 42 43 44
A C C C B D B D B B B
45 46 47 48 49 50 51 52 53 54 55
C A A B C C D B A C C
56 57 58 59 60 61 62 63 64 65 66
C A A B A D C C A A B
67 68 69 70 71 72 73
B C B D C D A

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