Section (A) : Inductive effect

A-1. Inductive effect involves:

(A) Delocalisation of cr-electrons (B) Partial displacement of a-electrons
(C) Oelocalisation of n-electrons (D) Displacement of lone pair electrons.

A-2. a. Select correct statement about I effect?

(A) I effect transfers electrons from one carbon atom to another.
(B) I effect is the polarisation of a bond electrons.
(C) I effect creates net charge in the molecule.
(D) I effect is distance independent.

A-3. Which of the following group shows +I-effect :

(A) -Br (B) -COOH (C) -OR (D)-COO-
A-4. Which of the following alkyl group has the maximum +I effect ?
(A)(CH,),CH- (B)(CH),C- (C) CH,CH,- (D)CH,-
A-6.a Decreasing -I effect of given groups is :
(i)-CN (ii)-NO, Oii)-NH2 (iv)-F
(A) iii> ii> i > iv (B) ii> iii> iv> i (C) iii> ii> iv>i (D)ii>i>iv>iii
A~. Which of the following is the strongest - I group :
+
(A)- N(CH,)3 (B)- NH3
+
(C)- S(CH,), (0)-F

Section (B) : Resonance Concepts, Conditions, Resonating Structures & Conjugation

B-1. Resonance is delocalisation of :
(A)• electrons (B) a electrons (C) a --1t electrons (D) None
B-2.a Resonance involves :
(A) Delocalization of n~lectrons along a conjugated system.
(B) Delocalization of lone pair along a conjugated system.
(C) Delocalization of negative charge along a conjugated system.
(D)AII are correct.
B-3. During delocalization, which statement is incorrect :
(A) Net charge remains same (B) Number of paired electrons remain same
(C) Number of unpaired electrons remain same (0) Energy of resonating structures always remains same

B-4. Resonance structure of the molecule does not have

(A) higher energy than their hybrid structure. (B) identical arrangement of atoms.
(C) the same number of paired electrons. (D) always equal contribution to the resonance hybrid.

B-5.a Which of the following species can not show resonance?

(A)o (B)o 8

(C)o
"
(D)o

B-6. Resonance is not possible in :

(A)6 (B)Q (C)CH, =CH-CI (O)Q

B-7. Which does not have conjugate system ?

(A) CH 2 = CHCI (B) CH 2 = CHCHO (C) CH 3 CH = CH 2 (0)0

B-6;,,. The compound which is not resonance stabilised

(A) CH 2=CH-CI (B)OO (C) CH 2=CH-CH2CI (D) 0

N
I
CH,

~- Which of the following is not acceptable as resonating structure:

e EB EB e
(A) CH,-rO (B) CH,=rO (C) CH,=tO (D) None of these
B-10. Which of the following pair is not pair of resonating structures?
0 •
(B) CH, = CH-0 & CH,-CH = 0

0
(C) CH,=CH--0-CH, & Cf½- CH = 0- CH3
"
"
(D) CHJ-C = O & CHJ-C a O "
B-11 . Which of the following structures are resonance structures ?
o-
/
& & CH, -C\._
'\CH

(C) (CHJ,CO & (D) CH,-CH=CH-CH, & CH,-CH,-CH=CH,

B-12.a. Among the given sets, which represents the resonating structure?

(A) H--C = ~&: and H-Q-c : N: "

(B) H-9 = C=N: and
0
H- 9 -C=N:
0
ffi e II ..
(C) H-C = N~; and H-C- N: (D) H-q-c=~ and H-~.J°=C=O:
B-13. In which of the following resonance is not possible?
(A) CH, =C=CH, (B) CH, = C =CH" (C) CH, =C = CH• (D)CH, =C= CH"

Section (C) : Mesomeric Effect

C-1. Which of the following group show +M effect?
(A) -CN (B) -0--NO (C) -CCI, (0)-CHO
C-2. Which of the following group show-M effect?

(A)-CMe, (B)-0-fO-R (C) -NH1-CH, (D)fO-R

C-3.
(A) r
Which of the following group show +M and -I effect ?
(B) t ° R (C)-0" (0)-0H

C-4. Which of the following group show +M > -I effect?

(A) -F (B) --a-!R (C) 1-R (D)-COOH

C-5. Which of the following groupshow-M and-I effect?

(A) -NO, (B) -NH, (C) -OH (0)-F

c~. +M and +I both effects are shown by :

(A) - QH (B) - NHCH, (C) - o• (D)-C(CHJ,
C-7. The weakest +M group of the given species is:
(A)-OCH, (B)-F (C) - I (D)-N(CHJ,
Section (D) : Stability of Resonating Structures and different species
0-1. Which one of the following is least stable resonating structure?

0
II
(A) NH,-C-0-CH,
e a? cf3
I f
(B) NH,=C-OCH, (C) NH,-2"-0CH, (D) NH,--C=rH,

D-2. Which of the following resonating structure is the least contributing structure?

o• 0 0
(A)~ (B)~ (C)~ (D)~

D-3.a HNCO (isocyanicacid) has following resonating structures:

H - N = C=O H-~-C = cf H-~ = C-cf

I II lil
The order of stablity is :
(A)l > Ill > II (B)l > Il > Ill (C) II > Ill > l (D) Il > l > Ill
D-4.a The correct stability order of the following resonanating structures is;

CH~=C=O
(I)
(A) (IV) > (I) > (Ill) > (II) (B) (11) > (IV) > (I) > (111) (C) (Ill) > (II) > (IV) > (I) (D) (I)> (IV)> (Ill)> (II)

D~. Which is the most stable resonating structure?

(A) ~ O ( B ) ~cf' ( C ) ~cf'

Section (E) : Steric Inhibition of Resonance (SIR Effect)

E-1."a Maximum extent of steric inhibition of resonance can be expected in

(A)~
(B)p-r< (C)Q,(
E-2. Select the correct statement about this compound.

~.
N ~ N O,
Br
(A)All three C-N bond length are same.
(B) C 1-N and C 3-N bonds length are same but shorter than C 5-N bond length.
(C) C 1-N and C 5-N bonds length are same but longer than C 3-N bond length.
(0) C 1-N and C 3-N bonds length are different but both are longer than Cs-N bond length.

Section (F) : Hyperconjugation

F-1.-is. In hyperconjugation there is overlap between :
(A) p-- and x-orbitals (B) 2x-orbitals (C) d-and-x-orttial (D) a -and p- orbitals
F-2. Which of the following cannot exhibit hyperconjugation -

(A)CH3CH:, 3 (C) CH3CH = CH2

(B) ~~ )CH
3

F-3. Which of the following alkenes will show maximum number of hyperconjugation fonns?
yH,
(A) CH, = CH, (B) CH,--CH=CH, (C) CH,--CH,--CH=CH, (0) CH,--CH--CH=CH,

F-4,,._ Arrange the stability of following

0 (JC CY
II III
(A)l<ll<III (B)ll<I< Ill (C)I < 111<11 (0)11<111<1

F-5.a. Which one of the following has inductive, mesomeric and hyperconjugation effect?
(A) CH,CI (B) CH, - CH= CH,

(C)CH CH= CH-C-CH 3 (0) CH, = CH-CH =CH,

' g
F-6. Which of the following group has the maximum hyperconjugation effect when attached to bezene ring?
(A) CH,- (B) CH,CH,- (C)(CH),CH-- (O)(CH,),C-

Section (G) : Concept of Aromaticity

G-1. Which out of the following is aromatic hydrocarbon?

(B)o Q
(C)
co (0)0 N
G-2.a Identify the aromatic compound ?

(A)O) (B)O::J (C) r o

(O)x
G-3. Aromatic compounds bum with sooty flame because :
(A) They have a ring structure of carbon atoms.
(B) They have a relatively high percentage of hydrogen.
(C) They resist reaction with oxygen of air.
(D) They have a relatively high percentage of carbon.

Section (H) : Applications of electronic effect

H-1 . The decreasing order of electron density on the ring is :
0
0
_,,CH,
r;::;y--N H, _,-CH,
H,N ~ C H,-C...,_
II
l8J NH n 0
CH,
II
Ill
(A) Ill> II> I (B) II> Ill> I (C) I> Ill> II (0) Ill> I> II
H·2.a Correct dipole moment order is

NH, (ajQ
Cl

(Q¢
Cl

(p)v
CH,
CH,
(A)p>q>r (B}r>q>p (C}q>r>p (D}p>r>q
H-3. Arrange following compounds in decreasing order of their dipole moment.
CH3-CH2--F CH3-CH2~
Ill IV
(A}IV>lll>I> II (B)IV>l>lll>II (C) I> Ill> IV> II (D)l>IV>lll>II

p p
H-4.a The stability order of alkene in following compounds is;

J) vO
(I} (II) 01~ OV)
(A} I< II< Ill< IV (B) 11< I< Ill< IV (C}ll<Ill<l<IV (D)ll<IV<l<III

PART - Ill : MATCH THE COLUMN

1.a Match the follO'Ning
Coulmn-1 Coulmn-11
(Compounds) (Characteristics)

<Al ~o (p) Mesomeric effect/ resonance

(B} Ph-CH=CH-CH3 (q) Inductive effect.

(C} (Q Hyperconjugative effect

NO,

Cl

(D}
A (s) Nonpolar
Cl,,UCI
(I} Polar
A-1. (B) A-2. (B) A-3. (D) A-4. (B) A-6. (D)
A-6. (A) B-1. (A) B-2. (D) B-3. (D) B-4. (D)

II-Ii. (A) II-Ii. (A) B-7. (C) B-3. (C) B-9. (B)

B-10. (A) B-11. (B) B-12. (B) B-13. (A) C-1 . (B)
C-2. (D) C-3. (D) C-4. (B) C-6. (A) C-41. (C)

C-7. (C) D-1. (C) D-2. (B) D-3. (A) D-4. (D)

D-6. (B) E-1. (C) E-2. (C) F-1. (D) F-2. (D)

F-3. (B) F-4. (C) F-6. (C) F-41. (A) G-1. (C)

G-2. (B) G-3. (D) H-1 . (A) H-2. (B) H-3. (D)

H-4. (A)

PART-Ill
1. (A) - p.q.r.t; (B) - p.q.r.t ; (C) - p.q.r,t; (D) - p,q,s
 PART -1: ONLY ONE OPTION CORRECT TYPE
1. '/'I. The most unlikely representation of resonance structures of p-nitrophenoxide ion is :

b,N«o b,N)>- ~N.P --o,N.-.:-o

(A)¢ (B)o (C)Q (0)¢

o- 0 o- 0
2. In which delocalisation of positive charge is possible?

(A)6
~H,
(B)~H (0)6 cP

3.a.
.
Decreasing order of potential energy of the following cations is :

OH OH
CH -~-N,,-CH, CH 3 -b=N,.....CH 3
l 'cHl 'CH~
(I) OQ OIQ
(A)ll>l>III (B)l>II> Ill (C)III> II> I (0)11>111>1

~-
4. Stability order of the following species ?

NH

or/ '\.s"
(T) (11) (TTT)

(A)l>ll>DI (B)ID>l>Il (C)IIl>ll>J (O)J>IU>Il

5. In which of the following first resonating structure is more stable than the second?

(A) c~,-CH=O (B) c~,-0-CH,

e EB e EB
(D) O-CH=CH2

6. Which of the following is incorrect for stability of structures.

I I
(A) CH3 - CH - CH = CH 2 > CH 3 - C=CH - CH 3 (B)
0- 0
8
0
II
< CH, -C-0
a

7. Least contributing resonating structure of nitroethene is :

+90 + +90
(A) CH, = CH - N( (B) CH, - CH - N(
o- o-
+ +,&O
(C)CH, -CH-N(
o-
8. Which of the following statement is correct ?

(A) In the dianion

&

0
g , if'

0
all the C-C bonds are of same length but C-0 bonds are of different length

(B) In the dianion, all C-C bonds are of same length and also all C-0 bonds are of same lengths
(C) In the dianion, all C-C bond lengths are not of same length
(D) None of the above
9. The decreasing order of bond length of C=C bond in the following compounds is:

H
,C D
0 H
,C
II
0 0
Ill IV
(A) II> I> IV> Ill (B)lll>I>Il>IV (C)IV>Il>I>III (D)IV>I>Il>III

10. Which of the following is correct about the following compound

8 1
7f"'Y)2
6~3
5 4
(Naphthalene)
(A) All the C-C bond length are same
(8) C 1-C 2 bond length is shorter than C 2-C 3 bond length
(C) C1-C2 bond length isgreaterthan C2-C3 bond length
(0) All the C-C bond length are equal to C-C bond length of benzene

11.a The correct order of +M effect of 'N' containing functional group on benzene ring, amongst the given compounds
is

0
II
C-CH,
0- N/' c-cH
II '
(IV) 0

(A)I > ll > IV > III (B)ll > I > IIl > IV (C)I > II > lll > IV (D)IV > lll > II > I

12. In which case the a-bond pair and 1t bond pair of electrons both are attraded in the same direction, (towards
same atom.) :
(A) H,C=CH-CI (B) CH,-CH,-NH, (C) H,C=CH-CH=O (D) H,C=CH--OCH,
13.a The correct stability order of given resonating structures is :

(A)I>Il>IIl>IV (B)IV>lll > ll>I (C)l=Il=IIl=IV (D)Il=lll>l=IV

14. The longest C- N bond length in the given compound is :

' CH, TH,

NN
=:xxN~
'>- I 1/ CH,
./ y uNzcH

(A)x (B)y (C)z (D)w

15. a. Select the correct order of heat of hydrogenation ?

(I)~ (II)~

(A)l>ll>lll>IV (B)IV>lll>ll>I (C) II > Ill > IV > I (0) II > Ill > I > IV

Ell
16. Hl C-CH-CH=CH1 does not involve :
(A) a,:, overlap (B) a-ot• overlap (C)pn--p,toverlap (O)p,,-dnovefiap

17. Stability of x-bond in following alkenes in the increasing order is:

CH 3-CH = CH - CH3 CH 3 - C = C-CH 3 CH,- C = CH, CHl -C = CH-CHJ

I I I I
CH, CH, CH , CH.,
(I) OQ (Ill) (IV)
(A)I <Ill< IV<II (B)I <II< Ill< IV (C) IV< Ill< 11<1 (0) II< Ill< IV< I

18.~

In this molecules, x-electron density is more on :

w~•~ (D)C, andc.

19. If the given compound is planar. Select the correct statement.

CB-CH,
(A) The boron is sp2hybridized and the p--orbital contains an unshared pair of electron
(8) The boron issp2hybridized and a hybrid orbital contains an unshared pair of electron.
(C) The boron in sp2 hybridized and hybrid orbital is vacant
(0) The boron is sP' hybridized and the p-<>rbital is vacant

20. The correct order of electron density in aromatic ring of following compounds is:

~OEt ~OEt ~COCH,

II Ill IV
(A)IV>lll>ll>I (B)l>ll>lll>IV (C)IV>ll>l>III (0)IV>ll>lll>I
 PART - II : SINGLE AND DOUBLE VALUE INTEGER TYPE
1."a. Among the given sets , how many of the following not represents the resonating structure :

(i)H-C ~ and H-0-C.-N

" e
(iQ H-O=C=N and f+-0-CoN

., e
(iii)H~--0 and Hj_N
e
Ov) H--0-C~N and H-N=C=O
e
"
(v) CH,--CH~ O
.
and CH 2 = CH-O
(vi) CH 2 = CH-NH 2 and
e
CH 2--CH = NH 2

(vii) CH,-k H, and CH ,XCH,

2. How many of the following species can show resonance .

0 0 606 0"
e

O 0--0",
CH, =CH-CI
Ell
0
CH,

3.a. How many groups (attached with benzene ring) can show +M effect?

0 6·6 6 ·o
II

4.
0 o· o
Identify the number of compounds in which positive charge will be delocalised?

0 6 0 66
"" "' "
'"
()Na,
I
H
5. In how many of the following cases, the negative charge is delocalised?

o~ ct~
~ H,

6 @
e

0
e e

0 Q 0 CH, - CH, - CH -
e e ,1-0
N'-.
08
e
CH 2 - F

6. In how many of the following compounds Hyperconjugation effed is observed -

H
(A) C,H,-CH = CH, (8) Ph-CH, (C) C,H, ~H,

e d H,
(D) CH,-CH-cH, (E)\0 (F)
CHJCHl

(G) CH,-CH,i-CH,-CH,
CH,
H, r
(H) CH,- - CH =CH, (I) CH, {'
-EH,
H,

.
1.-,.. How many of the following compounds is/are aromatic?
e
(i)o (ii)L (iii),6, (iv)L
N

(v)o (vi) c
2
(vii)o
s

(ix)D
I
(x)'y (xi) Q>0
H
8.a Total number of moelcules which are entiaromatic?

(a) AH• (b) AHe

'9
H H H H
Cydopropenyl Cyclopropenyl Cyclobutenyl
cation anion di-cation
 (e) 0 (g)6 (h)vV
•
Cyclopentadieny1
Tropylium cation
(Cycloheptatrienyl
cation)
cation

(i)~ OJ
o9 A'

[1 8J Am.Aeoe

9. Find the number of carbon atoms including the given structure which can have negative change in resonating
structures. (The structure with charge reperating are not accepted)
e
HC = C--C--CH=C=CH,

~C=N

CH,

10. Observe the following compound and write the number of hydrogen atom involved in hyperconjugation?

11.
E
Find the total number of positions where positive charge can be delocalized by true resonance
CH,
(!J µ~
CH,--CH--cH=CH---0 · (Exduding the given position)

PART - Ill : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. Which statement is/are true about resonance ?
(A) It decreases the energy of system.
(8) The hybridisation of atoms do not change due to resonance
(C) Resonance hybrid is more stable than any resonating structure.
(D) Resonanting structures can not be isolated at any temperature

2. Which of the following statement is incorrect about resonance ?

(A) The most stable structure explains all the characteristics of a species.
(B)AII resonating structures remain in equilibrium.
(C) Resonance hybrid has maximum similarity with most stable resonating structure.
(D) Resonance hybrid is real.
3.a. In which of the following pairs of compounds, will second structure have more contribution to resonance
hybrid than first?

(A)w&GJ
"
Q Q

. .
(C) F-y°H & F=y-cH
NHl NHl

4. In which of the following pairs of resonating structures first resonating structure is more stable than second?

¢.
o"'

0 N
e
(B)

N•
if 'r:J'

5. In which of the following compounds delocalisation of electrons and shifting of electron in the same direction?

(A)6
OH

(B) CH,-NH-NO,

H
I
(C) CH,=CH-CH=CH-NO, (D) H2N-C = CH2

6. Which of the following groups cannot participate in resonance with benzene :

(A)-COOH (B)COO" •
(C) -NH 3 (D)-COCI

7.a. Which of the following is/are correct :

(A) 0 is antiaromatic (B) is aromatic

(C) C)=<1 is aromatic (D)

O=O- is aromatic
8. Which of the following is/are correct statement :
0
II
o· CH,
~~H,>
(A) @•-density
@,

OH CN

(B) ~ ' > @ •- density

@,

Q. (X). cf:)
e

(C) all are aromatic

$
CN CN CN

(D) CN'@> ®'CN > dipole moment

CN
9.1>. The correct orders for bond length are :

(A)o CH,

l_) (a'>a) (B) CH,-C~NH, (b' = b)

b'II
@NH 2
(C) CH,-c".oNa (c > C') (D)~'(d>d')
c· II
0

PART - IV : COMPREHENSION
Read the following passage carefully and answer the questions.
Hydrogenation of unsaturated hydrocarbons is an exothermic readion. Due to hyperconjugation aOO resonance
the stability of unsaturated hydrocarbons increases and the increase in stability is more due to resonance.
Compound with same number of 1t-bonds and more stability has lower heat of hydrogenation.
Heat of fonnation is defined as the energy evolved when a molecule is formed from its atoms. For isomers the
more stable compound has higher heat of fom,ation.
1, The correct heat of hydrogenation order is :
(p) 1, 3-Pentadiene (Q) 1, 3-Butadiene
(r) 2, 3-Dimethyl-1,3-butadiene (s) Propadiene
(A)p>q>r>s (B)s>q>p>r (C)q>s>p>r (D)s>p>q>r
2. The order of heat of formation of the following molecules is :

H'c=c_,,cH, CH;·•·,
C=CH,
CH~ '-H CH;•''.,....
(I) (11) (IV)
(A)l>ll>lll>IV (B)II >Ill> IV> I (C)IV>ll>lll>I (D) IV> 111 > 11> I
 PART-I
1. (C) 2. (D) 3. (A) 4. (A) 5. (C)

6. (A) 7. (C) 8. (B) 9. (B) 10. (B)

11. (C) 12. (C) 13. (D) 14. (D) 15. (B)
16. (D) 17. (A) 18. (B) 19. (D) 20. (D)
 PART-II
1. 5(i, iii , iv, v, vii) 2. 8 (ii , iii, iv, vi , vii, viii, ix, xi) 3. 5 (i, ii, v, vi, ix)
4. S(i, iii, v, vi, vii) 5. 5(i, ii, iv, vi, ix) 6. 3 (B. C&G).
7. 6 (i, iv, v, vi, vii , x)
8.
Aromatic - a, c, g, h. i.j. k. Antiaromatic-b, d, e Nonaromatic-f

9. 6 10. 9 11 . 2

PART-Ill
1. (ABCD) 2. (AB) 3. (ABC) 4. (BC) 5._ (BC)
6._ (C) 7. (BO) 8. (AD) 9. (ABO)

PART-IV
1. (B) 2. (C)