47 GOC

CLASS : XI CHAPTER : GOC

EXERCISE - 1 : BASIC OBJECTIVE QUESTIONS

Nomenclature
(a) 4-methyl-2-pentyne
1. The correct IUPAC nomenclature for the following alcohol
is : (b) 4,4¢ -dimethyl-2-pentyne

(c) methyl isopropyl acetylene

(d) 4,4,4-trimethyl-1-butene
Ans. (a)
(a) 2-ethyl-2-butanol (b) 3-methyl-3-pentanol
(c) 3-ethyl-3-methyl-3-pentanol
(d) 1, 1-diethylanol
Ans. (b) Sol.

Sol.
4. The IUPAC name of the following compound is :

2. The IUPAC name of CH3C(CH3)2 CH2CH CH2 is :

(a) 2, 5, 6-trimethylheptane
(a) 2,2-dimethyl-4-pentene
(b) 1,3-isopropyl-3-methylpropane
(b) 4,4-dimethyl-1-pentene
(c) 2, 6, 3-trimethylheptane
(c) 1,1,1-trimethyl-3-butene
(d) 2,3,6-trimethylheptane
(d) 2-chloro-4,4-dimethylhexane
Ans. (d)
Ans.(b)

Sol.

Sol.
Lowest set of locants rule-(2, 3, 6)

The longest continuous chain containing the functional 5. The name of according to IUPAC
that gives the functional group the lowest possible number.

nomenclature system is :
3. The IUPAC name of CH3 — C CCH(CH3)2 is :
(a) 2,3-dibromo-1,4-dichlorobutene-2
 GOC 48

(b) 1,4-dichloro-2,3-dibromobutene-2
(c) dichlorobromobutene
(d) dichlorobromobutane Sol.
Ans. (a)

8. The IUPAC name of

Sol.
is :
(a) 2,2-diethyl pentanoic acid
(b) 2,4-dimethyl hexanoic acid
6. Name of the compound given below is : (c) 2-methyl-4-ethyl pentanoic acid
(d) 4-ethyl-2-methyl pentanoic acid
Ans. (b)

Sol.
(a) 2,3-diethylheptane (b) 3-methyl-4-ethyloctane
(c) 5-ethyl-6-methyloctane (d) 4-ethyl-3-methyloctane
Ans. (d)

9. The IUPAC name of is :

Sol.
(a) 3-propylpent-1-ene (b) 3-ethylpent-1-ene
(c) 4-ethylhex-1-ene (d) 3-ethylhex-1-ene
Ans. (d)
Longest chain rule + lowest set of locants rule

7. The IUPAC name of CH3CH2C(Br) CHCl is :

(a) 4-chloro-3-bromo but-3-ene
Sol.
(b) 2-bromo-1-chloro butane
(c) 2-bromo-1-chloro but-1-ene
(d) 2-bromo-2-ethyl-3-chloro propene Preference of + longest chain rule double bond.
Ans. (c)
10. The IUPAC name of the compound
 49 GOC

is : H—C C — CH CH2 is :
3 3
(a) 3-ethyl-4-methylhex-5-en-2-ol (a) sp – sp (b) sp2 – sp3
(b) 3-ethyl-4-ethylhex-1-en-5-ol (c) sp3 – sp (d) sp – sp2
(c) 3-ethyl-2-hydroxy-4-methylhex-5-ene Ans. (d)
(d) none of the above
Ans. (a)

Sol.

Sol.

14. Hybridized carbon atom used in the formation of the

compound CH3 — CH CH — CH2 — CH3 are :
-OH functional group is preferred to double bond.
(a) sp and sp3 (b) sp and sp2
(c) only sp (d) sp2 and sp3
11. The IUPAC name of the compound
Ans. (d)
(CH3)2 CH – CH = CH – CHOH – CH3 is :
(a) 5-methylhex-3-en-2-ol
(b) 2-methylhex-3-en-5-ol
(c) 2-hydroxy-5-methyl-3-hexene Sol.

(d) 5-hydroxy-2-methyl-3-hexene
Ans. (a)
15. In the hydrocarbon,

Sol. The state of hybridization of carbons 1,3,5 are in the

following sequence :
(a) sp, sp2, sp3 (b) sp3, sp2, sp
(c) sp2, sp, sp3 (d) sp, sp3, sp2
12. The suffixes for alcohols, aldehyes and ketones according Ans. (d)
to IUPAC system are respectively :
(a) -alc, -ald, -ket (b) -ol, -al, -ket
(c) -ol, -al, -one (d) -coh, -ald, -one
Sol.
Ans. (c)
Sol. Functional group Suffix
Alcohols -ol
Aldehydes -ol 16. Which of the following statements is true about hybridization ?
Ketones -ol (a) Hybrid orbitals frequently undergo linear overlaps
making sigma bonds.
Hybridisation (b) Hybrid orbitals frequently undergo lateral overlaps making
13. The hybridization of carbon atoms in C—C single bond of p-bonds. In other words, there are several compounds in
which p-bonds are formed using hybrid orbitals.
(c) Hybrid orbitals are molecular orbitals.
 GOC 50

(d) A hybrid orbital bigger in size makes shorter bond. (c) both terminal C-atoms are sp-hybridized while central C-
Ans. (a) atom is sp2-hybridized

Sol. Conceptual (d) none of these

17. Ans. (b)

(a) C1—C2 bond of this molecule is formed by

(a) sp3–sp2 overlap (b) sp2–sp3 overlap
(c) sp–sp2 overlap (d) sp2–sp2 overlap
Sol.
Ans. (c)

20. Carbon atoms in the compound (CN)4C2 are

Sol.
(a) sp hybridised (b) sp 2 hybridised
(c) sp and sp 2 hybridised
(d) sp, sp 2 and sp 3 hybridised
Ans. (c)
18. In which of the following compounds, C has used sp2 orbital
in making C—O bond ?

(a) (b) Sol.

(c) (d)
21. Number of p electrons present in naphthalene is
Ans. (c) (a) 4 (b) 6
(c) 10 (d) 14
Ans. (c)

Sol.

Sol.

19.

In this molecule (allene) 22. In which bond angle is the highest

(a) all three C-atoms are sp2-hybridized (a) sp 3 (b) sp 2

(b) both terminal C-atoms are sp2-hybridized while central (c) sp (d) sp 3d
C-atom is sp-hybridized Ans. (c)
 51 GOC

Sol. Bond angle is highest in sp because molecule will be linear Sol. Stability of carbocations will be decided on the basis of + I
effect of -CH3 group because inductive effect depends upon
(1800).
distance.

Inductive Effect 26.

23. Inductive effect of Cl atom operates in
Which of these groups has –I effect ?
(a)
(a) I (b) II
(b)
(c) III (d) all of these

Ans. (d)
(c)

(d) all of these

Sol.
Ans. (d)
Sol. Option (d) is correct. Partial charges will come due to - I
effect of - Cl group.
Þ N, Cl, I have tendency to attract electrons
\ showing -I effect.
24. Inductive effect of a —CH3 group operates

Resonance
(a) (b)
27. In which of the following molecules, all atoms are coplanar?

(c) (d) both (b) and (c)

(a) (b)

Ans. (d)

Sol. Option (d) is correct. + I will define stability.

25. Inductive effect of —CH3 group operates in

(c) (d)

(a) (b)
Ans. (a)

(c) (d) all of these 28. In which of the following molecules, –NO2 group is not
coplanar with phenyl ring ?
Ans. (d)
 GOC 52

30.
(a) (b)

The correct order of stability among these canonical

structures is
(a) I > III > II (b) III > I > II
(c) II > III > I (d) II > I > III
Ans. (b)
Sol. In II octet of carbon is (C+) is incomplete in I, III octet is
(c) (d) complete. So, II is least stable. In III negative charge is on
more electronegative atom. So, it will be most stable. So,
correct order is III > I > II

Ans. (c)
31.

29. In which of the following molecules, all atoms are not coplanar ?

(a)

(b)

(c)

(d)

Ans. (c)

Among these canonical structures of pyridine, the correct

order of stability is

Sol. (a) ( I = V) > (II = IV) > III (b) (II = IV) > (I = V) > III

(c) (I = V) > III > (II = IV) (d) III > (II = IV) > (I = V)
3
Because central carbon is sp - hybridized.
Ans. (a)
 53 GOC

Sol. In I and V, octet is complete and are identical. So, I and V are
most stable. In II and IV unlike charges are near. So, correct 34.
order is.

(I = V) > (II = IV) > III Which of the following statements is true about this molecule ?
(a) C1—C2 and C3—C4 bonds are of same length
(b) C1—C2 bond is shorter than C3—C4 bond
(c) C1—C2 bond is longer than C3—C4 bond
32.
(d) C1—C2 and C2—C3 bonds are of same length
Ans. (b)
The most stable canonical structure among these is Sol. C3-C4 double bond is in conjugation with both the double
(a) I (b) II bonds on either side but C1-C2 in only in conjugation with
C3-C4. So, bond length of C3-C4 will be longer.
(c) III (d) all are equally stable

Ans. (c)
35.

Among these compounds, which one has shortest C—Cl

Sol. bond ?
(a) I (b) II
(c) III (d) IV
Ans. (a)
In III octet is complete it is most stable as O is electronegative
atom. So, it will stabilize the +ve charge, which is far away
from it. So, II will be least stable.

Sol.
33. Heat of hydrogenation of cyclohexene is –28.6 kcal/mol and
that of benzene is –49.8 kcal/mol. Then resonance energy of
benzene will be
In I, resonance can occur so partial bond character will be
(a) 46 kcal/mol (b) 39 kcal/mol there. Hence, itwill have shortest C-Cl bond length.

(c) 36 kcal/mol (d) 30 kcal/mol

Ans. (c)

36.

Sol.

DHTh = 3 ´ (-28.6) = -85.8 kcal/mol

Resonance Energy = DHActual -DHTh= -49.8 -(-85.8) = 36.0 kcal/mol

 GOC 54

The stability order of these canonical structures is (c) (d)

(a) I > II > III (b) III > I > II

(c) I > III > II (d) II > III > I
Ans. (c)
Ans. (b)
Sol. In option (c), N is pentavalent which is not possible. Option
Sol. II will be least stable, because octet of C+ is incomplete. III (c) is correct.
will be more stable than I, because in III +ve charge is an N
which is less electronegative than O. so, correct order is III
39. Resonance structure of a molecules should have
> I > II.
(a) Identical arrangement of atoms
(b) Nearly the same energy content
37. In which of the following molecule the resonance effect is
not present ? (c) The same number of paired electrons
(d) All the above
Ans. (d)
(a) (b)
Sol. Option (d) is correct conceptual.

Electrophile/Nucleophile
(c) (d)
40. Which of the following species is an electrophile ?
(a) H (b) H
Ans. (b)
(c) both (a) and (b) (d) none of these
Sol. Option (b) is correct.
Ans. (a)
Sol. Electrophiles carry positive charge, hence are electron
deficient.
Option (a) is correct.

38. The most unlikely representation of resonance structure of

p–nitrophenoxide ion is : 41. Which of the following species is a nucleophile ?
(a) H2O (b) H3O

(c) both (a) and (b) (d) none of these

Ans. (a)
Sol. H2O has electron pair to donate. Option (a) is correct.
(a) (b)

42. Which of the following species is a nucleophile ?

(a) CH3O (b) CH3OH

(c) both (a) and (b) (d) none of these
Ans. (c)
Sol. Both CH3O- and CH3OH have electron pair to donate.
 55 GOC

Option (C) is correct.

45. Which of the following orbital diagrams represents the case
of hyperconjugation ?
43.

(a)

pyrrole (I) pyridine (II) aniline (III)

Which is/are correct statements ?
(a) I is more basic than II
(b) II is more basic than I and III
(c) III is more basic than II
(d) None of these (b)
Ans. (b)
Sol. In pyridine lone pair will not participate in resonance
because L.P. is present in perpendicular p-orbital so, L.P. is
completely available for donation. In pyridine and aniline
the L.P. will participate in resonance. So, pyridine is most
(c) both (a) and (b)
basic.
(d) none of these
Option (b) is correct.
Ans. (a)
Sol. Option (a) is correct
Hyperconjugation
44. Which of the following represents the case of
hyperconjugation ?
(a) (b)

46. Hyperconjugation occurs in

(c) (d) both (b) and (c)
(a) (b)

Ans. (b)
Sol. Option (b) is correct (c) (d) All of these
Option (a) is resonance
Option (c) is tautomerism Ans. (d)
Sol. All can show hyperconjugation.
Option (d) is correct.

47. Hyperconjugation occurs in

 GOC 56
(a) (b)
(a) CH CH2 (b) CH CH CH3
3 3

(c) CH CH2 CH2 (d) all of these

3

Ans. (d)
Sol. Option (d) is correct.

s (C – H), positive charge conjugation.

48.

How many hyperconjugable H-atoms does this molecule has ? (c) both (a) and (b)
(a) 0 (b) 2 (d) none of these
(c) 3 (d) 4 Ans. (a)
Ans. (d)

Sol.

Sol.

Hence, 4 hyperconjugable H-atoms are present. Option (d)

is correct.

49.

50. Diene Heat of Hydrogenation

Canonical structures due to hyperconjugation in this –54.1 kcal/mol

molecule can be written as I
–70.5 kcal/mol
II
–60.2 kcal/mol
III
Examine these dienes and their heat of hydrogenations. Now,
what will be the stability order among these dienes ?
(a) I > II > III (b) II > III > I
(c) I > III > II (d) II > I > III
Ans. (c)
Sol. Order of stability of dienes is,
 57 GOC

Conjugated > Isolated > Cumulated

(IV)
51.

The correct decreasing order of enthalpies of reaction for

producing carbocation is

Among these compounds, the order of heats of (a) DH1o > DH 2o > DH 3o > DH 4o
hydrogenation is :
(b) DH o4 > DH1o > DH o2 > DH 3o
(a) I > II > III (b) III > II > I
(c) II > I > III (d) II > III > I (c) DH 3o > DH o2 > DH1o > DH o4
Ans. (c)
(d) DH o2 > DH1o > DH o4 > DH 3o
Sol. I is conjugated double bond, Thus, heat of hydrogenation
is less than II, which is isolated double bond Thus, the Ans. (b)
order of heat of hydrogenation is II > I > III Sol. Least stable carbocation formation will lead to highest
enthalpy of reaction carbocation order is
Carbocation
52. Which of the following carbocation is least stable ?
Hence, order of enthalpy of reaction

D H04 > D H10 > DH20 > DH30

(a) (b) CH CH2 54. Which of the following is most stable

(c) CH2 CH CH2 (d)

Ans. (b)
Sol. Vinyl carbocations are least stable.

53. For the reactions

(I)
(a) I (b) II
(c) III (d) IV
Ans. (d)
(II) Sol. In IV, octet of each atom is complete.
Hence, Option (d) is correct.

(III) 55. The order of reactivity of the following alcohols towards

conc. HCl is :
 GOC 58

(I) stability of carbocation.

(II) (III)

(a) I > II > III (b) I > III > II

(c) III > II > I (d) III > I > II
Ans. (d)
Sol. The reaction will involve the formation of carbocation.
Hence, alcohol forming more stable cation will be more +M is stronger than Hyperconjugation and + I combined.
reactive. Hence, carbocation are Correct stability order.
III > II > IV > I

Carbanion

57.

Which of the following orders is correct for the stability of

these carbanions ?
Order follows,
III > II > I (a) I > II > III (b) III > II > I

(c) II > I > III (d) I » II » III

56. What is the correct order of stability of the given cations :
Ans. (a)

Sol. +I effect of alkyl group will decrease the stability of

carbocation. Hence, correct order is I > II > III

58.

Which of the following orders is correct for the stability of

these carbanions ?

(a) III > II > IV > I (b) I > II > III > IV (a) I > II > III (b) III > II > I
(c) III > I > II > IV (d) IV > II > III > I (c) II > III > I (d) II > I > III
Ans. (a)
Ans. (b)
Sol. Electron releasing group will decrease the stability of
carbocation and electron withdrawing will decrease the Sol. III and II can show resonance. So, I is least stable. In III,
negative charge can delocalize on 4 positions, but in II it
 59 GOC

can delocalize on only 2 position. So, III is more stable than
II.
Hence, correct order of stability is, III > II > I
Sol. Negative charge on more electronegative carbon atom will
stabilize the carbanion. So, more the % s character more
will be the electronegativity.
SP > SP2 > SP3

59.

So, correct order is

Which of the following orders is correct for the stability of III > II > I
these carbanions ?
(a) I > II > III (b) III > II > I Carbon free Radical
(c) III > I > II (d) II > I > III 61.
Ans. (d)

Sol. Electron with drawing groups will increase the stability of

carbocation.
Which of the following orders is correct for no-bond-
resonance energy of these radicals ?
(a) I > II > III (b) III > II > I
(c) III > I > II (d) II > III > I
Ans. (a)
Sol. Less the stability less the no-bond resonance energy.
So order is
I > II > III

Mesomeric effect work only at -o and -p positions. Hence,

order is 62.

II > I > III

60. Which of the following orders is correct for no-bond-

resonance energy of these radicals ?
Which of the following orders is correct for the stability of (a) I > II > III (b) III > II > I
these carbanions ?
(c) II > III > I (d) II > I > III
(a) I > II > III (b) III > II > I Ans. (c)
(c) II > I > III (d) III > I > II Sol. Correct order is less the stability less the II > III > I

Ans. (b)
 GOC 60

66.
63.

Which of the following orders is correct for no-bond-

resonance energy of these radicals ?
(a) I > II > III (b) III > II > I
(c) II > III > I (d) II > I > III
Ans. (c)
Sol. Conceptual

64. Which of the following statements is correct about methyl

group ? Among these, chain isomers are
(a) It stabilizes both carbocation and free radical equally (a) I and II (b) I and III
(b) it stabilizes a free radical more than a carbocation (c) II and III (d) all of these
(c) it stabilizes a carbocation more than a free radical Ans. (d)
(d) none of these Sol. All are chain isomers.
Ans. (c)
67.
Sol. Conceptual

Isomerism

65.

Among these, I is the chain isomer of

(a) II only (b) III only
(c) both (d) none of these
Ans. (a)
Which among these are stereo-isomers ?
Sol. I is chain isomer of II and position isomer of III.
(a) I and II (b) I and III
(c) II and III (d) all of these
Ans. (c)
Sol. II is cis and III is trans isomer. Option (c) is correct.
 61 GOC

68. Among these functional isomers are

(a) I and II (b) I and III
(c) II and III (d) Both (a) and (c)
Ans. (d)
Among these, positional isomers are Sol. I and III are alcohols. II is ether
(a) I and II (b) I and III
(c) II and III (d) all of these
Ans. (d)
Sol. -CH3 groups are at different positions with respect to each
other.
71.

69.
The tautomer of II is
(a) I (b) III
(c) both I and III (d) none of these
Ans. (c)
Sol. I and III can show tautomerism to form

72.

Among these III is the chain isomer of

(a) I only (b) II only
(c) both I and II (d) none of these
Ans. (c)
Which among these are tautomers ?
Sol. -OH is present in different chains.
(a) I and II (b) I and III
(c) II and III (d) None of these
70. Ans. (d)
OH Sol. II and III are position isomers. I is functional isomer of II
and III.

Isomerism
73. Which of the following will exhibit geometrical isomerism ?
 GOC 62

(a) 1–Phenylbutene–2–ene
(b) 3–Phenylbut–1–ene
(c) 2–Phenylbut–1–ene
Sol.
(d) 1, 1–Diphenylprop–1–ene
Ans. (a)

Sol.

74. Geometrical isomerism will be exhibited by 76. The simplest alkene which is capable of exhibiting
geometrical isomerism has
(a) Pent–1–ene
(a) 3 carbon atoms (b) 5 carbon atoms
(b) 3–Methylbut–1–ene
(c) 6 carbon atoms (d) 4 carbon atoms
(c) Pent–2–ene
Ans. (d)
(d) All of these compounds
Ans. (c)
Sol. Pent-1-ene
Sol.

It will not show geometrical isomerism

3-Methyl but-1-ene 77. Which of the following compounds can exhibit geometrical
isomerism ?
(a) Hex–1–ene (b) 2–Methylpent–2–ene
(c) 3–Methylpent–1–ene (d) Hex–2–ene
Ans. (d)
It will not show geometrical isomerism
Pent-2-ene
Sol.

It will show geometrical isomerism 78. Which one of the following compound will show
geometrical isomerism ?
75. Which of the following compounds can show geometrical
isomerism ? (a) (b)
(a) Vinyl chloride (b) 1, 1–Dichloroethene
(c) 1, 2–Dichloroethene (d) Trichloroethene
Ans. (c)
(c) (d)

Ans. (b)
 63 GOC

Sol. In (a), (c) and (d) the similar atoms (groups) are on one or geometrical isomers of each other?
both of the carbon atoms.

(a)
79. How many open chain structural isomers of compound with
molecular formula C6H12 show geometrical isomerism ?
(a) 2 (b) 3
(c) 4 (d) 5 (b)
Ans. (c)
Sol. C6H12 It is an alkene and it’s degree of unsaturation is 1.
For CxHy type molecule, (c)
D.U.= x + 1 - y/2
So, for C6H12
(d)
12
D.U = 6 + 1 - =1
2
So, It will contain one double bond or one ring . Ans. (c)

It’s open chain structures are, Sol. Only C will show geometrical isomerism option c is correct.
82. The compound C4H10O can show
(a) metamerism (b) positional isomerism
(c) functional isomerism (d) all types
Ans. (d)
Sol. C4H10O can represent alcohol and ether. Ether shows
metamerism, ether and alcohol show functional isomerism
, and alcohol shows position isomerism.

83. Isomers are the compounds having the

(a) same molecular formula but different physical and/or
chemical properties.
(b) same structural formula but different molecular formulae
(c) same chemical properties and physical properties
Only (b), (c), (f) and (i) can show geometrical isomerism.
(d) same physical properties but different chemical properties.
Option (c) is correct.
Ans. (a)
Sol. Isomers have same molecular formula but different
80. Which of the following can exist as cis and trans isomers ?
physical and/or chemical properties. Option a is correct.
(a) (b)
(c) (d) 84. Which of the following has maximum enol content ?
Ans. (c)
Sol. Structure having similar atoms (groups) are on one or (a) Acetaldehyde (b)
both of the carbon atoms will not show geometrical
isomerism.
(c) Acetylacetaldehyde (d)
81. Which of the following pair of structures represent
 GOC 64
Ans. (c)
Sol. condition for tautomerism®a-carbon must be SP3 hybridized.

Sol.

Order of enol content is

b-keto aldehyde > b-diketones > aldehydes > ketones
(c) (d) (a) (b)

Option c is correct.

85. Which is a pair of geometrial isomers ?

(a) I and II (b) I and III

(c) II and IV (d) III and IV
Ans. (c)
Sol. (I) will not show geometrical isomerism. II and IV are
geometrical isomerism.

86. Enolic form of the given keto compound is

(a) (b)

(c)

(d) It will not show tautoisomerism

Ans. (a, c)
 57 GOC

EXERCISE - 2 : PREVIOUS YEAR AIEEE (JEE MAINS) QUESTIONS

N V
H2 SO4 N 60 ml
Sol. 5
NaOH N 20 ml
10
1.
( ngmep )H2SO4 = ( ngmep )NaOH + ( ngmep )NH3
1 60 1 20
Among these cations, which of the following orders is
´ = ´
5 1000 10 1000
+ ngmep ( )NH3
correct for their no-bond-resonance energy ? (2015)
5
(a) I > II > III (b) III > II > I
( ngmep )NH3 = 500 =1
100

( )NH3 = 1 100
(c) I > III > II (d) III > I > II
Ans. (c)
(nmol )N = ( nmol )NH3 = ngmep

Sol. No-bond Resonance (Hyper conjugation)

14
µ -Hydrogen (Mass)N = = 0.14 g
100

0.14
% of N = ´ 100 = 10%
1.4

3. The order of stability of the following carbocations

(2013)

2. For the estimation of nitrogen, 1.4 g of an organic

compound was digested by Kjeldahl method and the
M
evolved ammonia was absorbed in 60 mL of sulphuric
10

M
acid. The unreacted acid required 20 mL of sodium
10
hydroxide for complete neutralization. The percentage of
nitrogen in the compound is (2014)
(a) 5% (b) 6%
(c) 10% (d) 3%
(a) III > II > I (b) II > III > I
Ans. (c)
(c) I > II > III (d) III > I > II
 GOC 58
Ans. (d)
Sol. Greater the number of resonating structures a carbocation
possess, greater is its stability. (a) (b)

4. How many chiral compounds are possible on

monochlorination of 2-methyl butane ? (2012)
(a) 2 (b) 4 (c) (d)
(c) 6 (d) 8
Ans. (a) Ans. (a)
Sol. Non-aromatic compound

6. The correct order of increasing basicity of the given

conjugate bases (R = CH3) is (2010)
Sol. (a) RCOO < HC = = C < R < NH 2

(b) R < HC º C < RCOO < NH 2

(c) RCOO < NH 2 < HC º C < R

(d) RCOO < HC º C < N H 2 < R

Ans. (d)

Sol. RCOO < HC º C < NH2 < R

Negative charge on less electronegative atom is rustable.
Therefore, basicity increases.

7. Arrange the carbanions,

in order of their
decreasing stability (2009)

(a)

(b)

(c)

Out of four possible isomers only I and III are chiral. (d)

Ans. (c)
5. The non-aromatic compound among the following is (2011)
Sol. The groups having +I effect decrease the stability while
groups having -I effect increase the stability of
 59 GOC

carbanions. Benzyl carbanion is stabilized due to

reaonance. Also out of 20 and 30 carbanions, 20 carbanions
are more stable, thus the decreasing order of stability is.
Sol.
CCl3 > C6H5 CH2 > (CH3 )2 CH > (CH3 )3 C.

3-ethyl-4, 4-dimethylheptane
8. The IUPAC name of neopentane is (2009)
(a) 2-methylbutane (b) 2, 2-dimethylpropane 11. The IUPAC name of the compound shown below is
(c) 2-methylpropane (d) 2,2-dimethylbutane (2006)
Ans. (b)

Sol.

(a) 2-bromo-6-chlorocyclohex-1-ene

Neo- pentane or 2, 2- dimethyl propane (b) 6-bromo-2-chlorocyclohexene

(c) 3-bromo-1-chlorocyclohexene

9. The correct decreasing order of priority for the (d) 1-bromo-3-chlorocyclohexene

functional groups of organic compounds in the IUPAC Ans. (c)
system of nomenclature is (2008)
(a) —COOH, —SO3H, —CONH2, — CHO
(b) —SO3H, —COOH, —CONH2, —CHO
(c) —CHO, —COOH, —SO3H, —CONH2
(d) —CONH2, —CHO, — SO3H,—COOH Sol.
Ans. (a)
Sol. The order of preference of functional groups is as follows:

-SO3H > -COOH > -COOR > -COX > -COCl > -CONH2 3 - bromo - I - chlorocyclohexene

12. The increasing order of stability of the following free

radicals is (2006)

(a)

(b)

(c)
10. The IUPAC name of is
(d)
Ans. (a)
(a) 1, 1-diethyl-2, 2-dimethylpentane
Sol. On the basis of hyper conjugation effect of the alkyl
(b) 4, 4-dimethyl-5, 5-diethylpentane
groups, the order of stability of free radical is as follows:
(c) 5, 5-diethyl-4, 4-dimethylpentane
tertiary > secondary > primary.
(d) 3-ethyl-4, 4-dimethylheptane
Ans. (d) Benzyl free radicals are stabilized by resonance and hence
 GOC 60
are more stable than alkyl free radicals. Further as the 15. Due to the presence of an unpaired electron, free
number of phenyl group attached to the carbon atom radicals are (2005)
holding the odd electron increases, the stability of a free
(a) cations (b) anions
radical increases accordingly.
(c) chemically inactive (d) chemically reactive
g g g g
i.e.(CH3 )2 CH < (CH3 )3 C < (C6H5 )2 CH < (C6H5 )3 C Ans. (d)
Sol. Free radicals are highly reactive due to presence of an
unpaired electron. They readily try to pair-up the odd
13. The correct order of increasing acid strength of the electrons.
compounds (2006)
(A) CH3CO2H (B) MeOCH2CO2H
16. Among the following acids which has the lowest pKa
value ? (2005)
(C) CF3CO2H (D) is
(a) CH3CH2COOH (b) (CH3)2CH—COOH
(c) HCOOH (d) CH3COOH
(a) B < D < A < C (b) D < A < C < B
Ans. (c)
(c) D < A < B < C (d) A < D < C < B
Sol. Lowest pKa ® More Ka ® More acidic
Ans. (c)

Sol.
More stable the amino is more the acidic strength
\ Lowest pKa value

17. The decreasing order of nucleophilicity among the

nucleophiles

More the stability of amino, more will be acidity (A) (B) CH3O–
D<A<B<C
(C) CN–

14. The number and type of bonds between two carbon

atoms in calcium carbide are (2005) (D) (2005)
(a) two sigma, two pi (b) two sigma, one pi
(c) one sigma, two pi (d) one sigma, one pi
(a) (C), (B), (A), (D) (b) (B), (C), (A), (D)
Ans. (c)
(c) (D), (C), (B), (A) (d) (A), (B), (C), (D)
Sol. Ca2 C2 C22- Ans. (b)
Sol. Strong bases are generally good nucleophile. If the
- -
CºC nucleophilic atom or the centre is the same, nucleophilicity
parallels basicity, i.e. more basic the as well as
nucleophilicity order is
1 s bond

2 p bond
 61 GOC

Sol.

Now CN- is a better nucleophile than CH3O- Hence

decreasing order of nucleophilicity is.

21. Rate of the reaction

18. The reaction

is fastest when Z is (2004)

is fastest when X is (2005) (a) Cl (b) NH2
(a) OCOR (b) OC2H5 (c) OC2H5 (d) OCOCH3
(c) NH2 (d) Cl Ans. (a)

Ans. (d)

19. The IUPAC name of the compound (2004) Sol.

is Cl Cl
2P 3P
(a) 3, 3-dimethyl-1-hydroxy cyclohexane In a chlorine, 2P-3P does not goes effective overlapping
(b) 1, 1-dimethyl-3-hydroxy cyclohexane after resonance.

(c) 3, 3-dimethyl-1-cyclohexanol
22. The IUPAC name of CH3COCH (CH3)2 is (2003)
(d) 1, 1-dimethyl-3-cyclohexanol
(a) isopropylmethyl ketone
Ans. (c)
(b) 2-methyl-3-butanone
(c) 4-methylisopropyl ketone
20. Which one of the following does not have sp 2
hybridised carbon ? (2004) (d) 3-methyl-2-butanone
(a) Acetone (b) Acetic acid Ans. (d)
(c) Acetonitrile (d) Acetamide
Ans. (c)
 GOC 62

Sol.
Sol.

3-methyl-2-butanone

25. Underlined carbon is sp 3 hybridised in (2002)

23. In the anion, HCOO– the two carbon-oxygen bonds are
found to be of equal length. What is the reason for it ? (a) (b)
(2003) (c) (d)
(a) Electronic orbits of carbon atom are hybridised Ans. (b)
(b) The bond is weaker than the bond
–
(c) The anion, HCOO has two resonating structures
(d) The anion is obtained by removal of a proton from
the acid molecule
Ans. (c) Sol.

Sol.

26. In the following benzyl/allyl system

-
HCOO has two resonating structures

24. Which of the following compounds has incorrect IUPAC

nomenclature ? (2002) (R is alkyl group)
decreasing order of inductive effect is (2002)
(a)
(a) (b)
(b)
(c)
(d)
(c) (d)
Ans. (a)

Sol.
Ans. (d)
Inductive Effect

30 C > 20 C > 10 C

(CH3 )3 C - > (CH3 )2 C - > CH3 CH2 -

 63 GOC

27. Following reaction

(CH3)3CBr + H2O (CH3)3COH + HBr is an example
of (2002)
(a) elimination reaction (b) free radical substitution
(c) nucleophilic substitution
(d) electrophilic substitution
Ans. (c)

Sol. (CH3 )3 C - Br + H2O ¾¾

® (CH3 )3 COH + HBr
Nucleophilic substitution reaction
 GOC 60

EXERCISE - 3 : ADVANCED OBJECTIVE QUESTIONS

1. All questions marked “S” are single choice questions
2. All questions marked “M” are multiple choice questions
3. All questions marked “C” are comprehension based questions
4. All questions marked “A” are assertion–reason type questions
(A) If both assertion and reason are correct and reason is the correct explanation of assertion.
(B) If both assertion and reason are true but reason is not the correct explanation of assertion.
(C) If assertion is true but reason is false.
(D) If reason is true but assertion is false.
5. All questions marked “X” are matrix–match type questions
6. All questions marked “I” are integer type questions

1. (S) The correct arrangement of the relative stability of the

three carbocation is :

(a) I > II > III (b) III > II > I

(c) I > III > II (d) III > I > II

Ans. (d)
Correct order is,
Sol. Electron withdrawing groups decrease the stability of
carbocation. -Cl can show only +M and -I effects. So, it III > I > II
is -I- effect will depend upon distance from positive
charge.
2. (S) Relative stabilities of the following carbocation will be
So, order of stability is, in order :
 61 GOC

So, correct order is,

IV > III > II > I
Option a is correct.

(a) I < II < III < IV (b) IV < III < II < I
4. (S) Which of the following is most likely to undergo a
(c) IV < II < III < I (d) II < IV < III < I favourable hydride shift ?
Ans. (c)
(a) (b)
Sol. IV can not show resonance but hyperconjugation.
ethers can show resonance so, IV will be least stable.

(c) (d)

Ans. (a)

Sol.

So, option (a) is correct.

So, correct order is,

I > III > II > IV 5. (S) Which of the following options is the correct order of
relative stabilities of cations as written below (most
Option c is correct. stable first) ?

3. (S) Consider the following structures

(I)
(I) (II)

(II)
(III) (IV)
The correct sequence of these carbocations in the
decreasing order of their stability is (III)

(a) IV, III, II, I (b) I, II, III, IV

(c) IV, II, III, I (d) I, III, II, IV (a) I > II > III (b) II > III > I
Ans. (a) (c) III > I > II (d) I > III > II

Sol. I is least stable (Vinyl carbocation). IV and III can show Ans. (a)
resonance but in IV positive charge can delocalize on Sol. I can show resonance. II can show hyperconjugation,
7-posotions. So, IV > III. But II can show III can show +I-effect.
hyperconjugation. So, order of stability is, I > II > III.
 GOC 62

6. (S) What is the decreasing order of stability (most stable

® least stable) of the following carbocations ?
(c)

(d)

Ans. (d)
(a) 3 >2 > 1 > 4 > 5 (b) 3 > 2 >5 > 4 >1 Sol. In option d conjugation is present
(c) 1 » 4 > 2 » 5 > 3 (d) 3 > 1 » 4 > 2 » 5
Ans. (b)

8. (S) Which carbocation is the most stabilized ?

(a) (b)

(c) (d)

Sol. Ans. (c)

Sol. In option c conjugation is present

So, option c is correct.

9. (S) Which of the following carbocation is most stable ?

Correct order is
3>2>5>4>1
Option b is correct.
(a) (b)

7. (S) Which of the following is the most stabilized

carbocation?

(c) (d)
(a) Ans. (c)
Sol. In option c conjugation is present
L.P. - vacant orbital
So, it will perform resonance.
Option c is correct.
(b)
 63 GOC

12. (S)

10. (S)
Rearrangement in this carbocation will produce

(a)

(b)

(c) both (a) and (b) (d) none of these

Which of the following orders is correct for the stability Ans. (b)
of these carbocations ?
Sol. Hydride shift is preferred to methyl shift. So,
(a) I > II > III (b) III > II > I rearrangement will form 30 carbocation
(c) II > III > I (d) III > I > II Option b is correct.
Ans. (a)
Sol. Correct order is
13. (S)

Regarrangement in this carbocation will produce

(a)

Option a is correct.
(b)

(c) both (a) and (b) (d) none of these

11. (S) Ans. (a)
Sol. Methyl shift will be done which will result in the
formation of 30 carbocation.
Option a is correct.

14. (S)
Which of the following orders is correct for the stability
of these carbocations ?
(a) I > II > III (b) III > II > I
(c) II > I > III (d) II > III > I
Ans. (d)
Sol. Positive charge on bridged carbon is unstable. Thus, Which of the following orders is correct for the stability
the order of stability is of these carbanions ?
II > III > I. (a) I > II > III (b) III > II > I
Option d is correct. (c) II > III > I (d) II > I > III
Ans. (d)
 GOC 64

Sol. In II, carbocation is in conjugation with

But in I, carbocation competes with lone pair of O for

resonance. So, correct order is, II > I > III
Option d is correct. Sol.

15. (S) Which of the following is least stable ?

Electron withdrawing groups increase the stability of

carbocation.
So correct order is,
II > I > III
Option c is correct.

(a) I (b) II
(c) III (d) None 17. (S) The correct order of stability of the three isomeric carbanions
Ans. (b) is:

Sol. In I and III, Nitrogen holds negative charge in it is

resonance structures. Negative charge on most
electronegative atom is more stable. But in II it is not
possible. Hence, II is least stable.
Option b is correct.

16. (S) Arrange the following in decreasing order of stability.

(a) I > II < III (b) I > III > II
(c) II > I > III (d) II > III > I
Ans. (d)
Sol. So, correct order is,
II > III > I

(a) I > II > III (b) I > III > II

(c) II > I > III (d) II > III > I
Ans. (c)
 65 GOC

19. (S)

Whcih of the following no-bond-canonical structures

is correct for this radical ?

(a)

18. (S) The three carbanions follows which order of stability

(b)

(a) I > II > III (b) I > III > II

(c) II > I > III (d) II > III > I
Ans. (b)

(c)

Sol.
(d) none of these
Ans. (a)

Sol.

Electron withdrawing groups increase the stability of

20. (S) Rank the following compounds in order of decreasing
the carbanion.
acid strength (most acidic ® least acidic).
Correct order is I > III > II
 GOC 66

Sol.

(a) 2 > 4 > 1 > 3 (b) 1 > 3 > 4 > 2 So, strongest acid is

(c) 3 > 1 > 2 > 4 (d) 3 > 1 > 4 > 2

Ans. (d)

Sol.

22. (S) Arrange following compounds in decreasing order of

basicity.

Electron withdrawing groups increase the acidity order

of acidity is, 3 > 1 > 4 > 2
Order d is correct. (a) IV > I > III > II (b) III > I > IV > II
(c) II > I > III > IV (d) I > II > III > IV
21. (S) Which of the following is strongest acid ? Ans. (d)
Sol. In II L.P is not involved in resonance. In I, due to -I
effect. In III and IV due to resonance. In IV L.P.
decolalization gains aromaticity.

(a) (b) So, option c is correct.

23. (S)

(c) (d)

Ans. (a)

Which of the following orders is correct for the basic-

strength of these compounds ?
 67 GOC

(a) I > II > III (b) III > II > I

(c) I > III > II (d) II > I > III

Ans. (c) (c) (d)

Ans. (a, b, c)
Sol. Sol. In all options resonance can be observed due to
conjugation. Hence partial double bond character will
be there which will decrease the bond order and increase
In aniline L.R. is involved in resonance. So, option c is the bond length.
correct. Options a, b and c are correct.
Electron density is more at nitrogen.

So, option c is correct. 26. (A) Assertion : Tropylium cation is more stable than

24. (M) Br has low reactivity in because : Reason : It is stabilized by both resonance effect and
inductive effect.
(a) the bond has a partial double bond
(a) A (b) B
character
(c) C (d) D
(b) of the +M effect of bromine
Ans. (c)
(c) Br is electronegative
Sol. Tropylium cation is more stable than (CH3)3 C+ because
(d) None of the above tropylium cation is aromatic in nature which is very
most stable. So, assertion is true but reason is false.
Ans. (a, b)
Option c is correct.

Sol.
27. (A) Assertion : The carbocation CF3 CH2 is less stable
than CF3 .
resonance is observed, due to which partial double
bond character will be there (+M effect of bromine). So,
Reason : In case of CF3 CH2, CF3 is strong electron
bond will become strong. Option a and b are correct.
withdrawing, therefore increases +ve charge whereas in
CF3 , lone pair of ‘F’ overlap with vacant p-orbital of
25. (M) Which of the following have larger C—O bond length carbon reducing +ve charge by pp - pp bonding or back
bonding.
(a) A (b) B
than C—O bond length of
(c) C (d) D
Ans. (a)

Sol.

(a) (b) So, option a is present.

28. (A) Assertion : The acetate ion is a weaker base than the
ethoxide ion.
Reason : In carboxylic acids, the carbonyl group is
 GOC 68

polarized and so the carbon of the carbonyl group bears

a partial +ve charge.
(a) A (b) B
Sol.
(c) C (d) D
Ans. (b)
L.P. of N2 will be busy in resonance, but L.P. of N1 will
be more basic.
Option b is correct.

Sol.
30. (S) Correct order of basicity of various nitrogen in

Acetate ion is resonance stabilized so, negative charge

will participate in resonance. It will not be available for
donation. So, acetate ion is weaker base.
Option b is correct.

29. (S) Which is the major product of the following reaction ?

(a) 1 > 2 > 3 (b) 2 > 1 > 3
(c) 2 > 3 > 1 (d) 3 > 2 > 1
Ans. (c)

Sol.
(a)

N1 will be least basic because it is L.P. will participate in

resonance on both sides. In N2 no, resonance is present
so it will be most basic. In N3 resonance is present but
two ethyl groups will provide electrons through +I
(b) effect.
So, option c is correct.

31. (S) Aniline is weaker base than ethyl amine. This is due to
(c)
(a) – I effect of NH2 in aniline
(b) – R effect of NH2 in aniline
(c) + I effect of NH2 in aniline
(d) + R effect of NH2 in aniline
(d)
Ans. (d)

Ans. (b)
 69 GOC

(III) (CH3)N

Which of the following orders is correct for the basic-

strength of these amines in polar solvents (e.g., –H2O) ?

(a) I > II > III (b) III > II > I

Sol.
(c) II > I > III (d) II > III > I

Ans. (c)

In aniline L.P. is involved in resonance so L.P. will not Sol. Order is decided on the basis of
available due to +R effect of -NH2 in aniline.
a) solvation
Option d is correct.
b) Inductive effect

c) steric effect
32. (S) Which of the following is strongest acid ?
Option c is correct.
(a) HCOOH (b) CH3COOH

(c) (d)
35. (S) (I) (II) (III)

Ans. (a)
Which of the following orders is correct for the basic-
Sol. +I and +M -effects decrease acidity of carboxylic acids.
strength of these anilines ?
Option a is correct.
(a) I > II > III (b) III > II > I

(c) II > I > III (d) I > III > II

33. (S) (I) CH3NH2 (II) (CH3)2NH (III) (CH3)3N
Ans. (d)
Which of the following orders is correct for the basic-
strength of these 1º, 2º and 3º amines in gas phase ? Sol. Electron releasing group will increase the basic strength
of aniline. In -Cl, -I effect dominates. So correct order is
(a) I > II > III (b) III > II > I I > III > II.
(c) II > I > III (d) II > III > I Option d is correct.
Ans. (b)

Sol. Electron releasing groups increase the basic strength. 36. (S)
Alkyl groups exert +I-effect.

So, order of basic strength. Which of these groups has –I effect ?

III > II > I (a) I (b) II

Option b is correct. (c) III (d) all of these

Ans. (d)

34. (S) (I) CH3NH2 (II) (CH3)2NH

 GOC 70

Sol.

Can exert -I effect. Option d is correct.

37. (S)

Which of these groups has +I effect ?

(a) I (b) II

(c) III (d) all of these

Ans. (a)

Sol. Comprehension

Hyperconjugation is no bond resonance. It involves s

Exert -I effect due to electronegative carbon atoms.
Option a is correct.
38. (M) Which of the following alkenes are more stable than
electrons of C—H bond. Greater the number of C — H
bonds (a-hydrogen atoms w.r.t. double bond) more will
be hyperconjugative structures, more will be stability.
Heats of hydrogenation of alkenes are affected by
hyperconjugative effects. Greater the hyperconjugative
structures, lower will be the heat of hydrogenation.

39. (C) Which of the following is incorrect hyperconjugative

structure ?

(a) (b)
(a) (b)

(c) (d)

(c) (d)

Ans. (a, b, c, d)

Sol. Alkene with more number of µ-Hatoms will be more stable.

 71 GOC

Ans. (c)

Sol.

Option c is correct.

40. (C) Which of the following has highest heat of

hydrogenation?

(a) CH 2 CH 2 (b) But-l-ene Comprehension

(c) Isobutylene (d) Tetramethyl ethylene When (C—H) s electrons are in conjugation to pi bond,
this conjugation is known as hyperconjugation : For
Ans. (a) any compound to show hyperconjugation

Sol. Greater the hyperconjugative structures (or greater - µH's), 2

(i) Compound should have one sp -hybridised carbon.

(ii) a-carbon with respect to sp should be sp

2 3
lower will be the heat of hydrogenation.
(iii) a-carbon should contain at least one hydrogen atom.

No. of a-carbon µ stability of cation and alkene.

42. (C) Which of following cations is hyperconjugation destabilized ?

(a) (b)

(c) (d)
41. (C) Which of the following has highest heat of combustion ?

(a) Isobutylene (b) But-l-ene

Ans. (d)
(c) Tetramethyl ethylene (d) But-2-ene

Ans. (b)
Sol.
Sol. Alkene with minimum number of µ -H atoms will

have highest heat of combustion.

 GOC 72

Sol. More the number of conjugative µ -H atoms

more will be electron density.

43. (C) Which of following alkenes is most stabilized ?

(a) (b)

(c) (d)

Ans. (c)

45. (S) Which of the following alkenes will exhibit geometrical

Sol. isomerism ?

(a) CH3–CH2–CH2–CH = CH2

(b) CH3–CH2–CH = CH–CH3

44. (C) Which of following alkyl benzene has maximum electron (c) CH3–CH2–CH = CH–CH2–CH3
density ?
(d) both (b) and (c)

Ans. (d)

(a) (b) Sol.

Different groups or atoms on both carbon atoms.

Different groups or atoms on both carbon atoms.

(c) (b)

46. (S) CH2=CH–CH=CH–CH=CH–CH3

How many geometrical isomers of this compound are

Ans. (a) possible ?
 73 GOC

(a) 2 (b) 3

(c) 4 (d) 8

Ans. (c)

Sol.

No. of geometrical isomers N = 2n

Sol.
n ® no. of double bond n = 2.

Where geometrical isomerism is possible.

N = 22 = 4

Option c is correct.
Only 2 geometrical isomers are possible

Option b is correct.
47. (S) CH3–CH2–CH=CH–CH=CH–CH3

How many geometrical isomers of this compound are

possible ? 49. (S) Number of which of the following isomers is always infinite ?

(a) 2 (b) 3 (a) Geometrical isomers

(c) 4 (d) 8 (b) Optical isomers

Ans. (c) (c) Conformational isomers

(d) Structural isomers

Sol.
Ans. (c)
N = 22
=4 Sol. Conformation will have infinite number of isomers.

Option c is correct.

48. (S) 50. (S) Which of the following compounds will exhibit confor-
mational isomerism ?

(a)
How many geometrical isomers of this cyclodecene are
possible ? (b)
(a) 0 (b) 2
(c) (d) all of these
(c) 3 (d) 4

Ans. (b)
Ans. (d)
 GOC 74
–
(B) — O (Q) +M effect
(C) — O — CH3 (R) +I effect
(D) C N (S) –I effect
Ans. (A – P, S; B – Q, R; C – Q, S; D – P, S)
Sol. A-P, S; B-Q, R; C-Q, S; D-P, S

Sol.

51. (S)
53. (X) Match the Column I and II (Matrix)

(A) (P) Pyramidal structure

(B) (Q) Planar geometry

(C) (R) Electrophile

(D) Singlet carbene (S) Nucleophile

Ans. (A – Q, R; B – P, S; C – Q, R; D – Q, R)

These two conformers exist in a state of dynamic

equilibrium. Which one is more stable ?
Sol.
(a) I (b) II
(c) Both are equally stable
(d) It is not possible to compare them for stability
Ans. (a)
Sol. Fully eclipsed form will be less stable due to repulsion 54. (A) Assertion : A mixture of o-nitrophenol and p-nitrophenol
between group or atoms. can be separated by steam distillation.
So, option a is correct. Reason : p-Nitrophenol is steam volatile while o-
nitrophenol is not steam volatile.

52. (X) Match the Column I and II (Matrix) (a) A (b) B

(A) — NO2 (P) –M effect (c) C (d) D

Ans. (c)
 75 GOC

Sol. A mixture of P-nitrophenol and o-nitrophenol can be following compound ?

separated by distillation. The o-nitrophenol is steam
volatile, and the para isomer is not volatile. P-
nitrophenol on account of larger distance between the
two groups (OH and NO 2 ) does not show any
interamolecular hydrogen bonding whileortho isomer
will show

(a) All three C—N bonds are of same length

(b) C1 — N and C3 — N bonds are of same length but

shorter than C5 — N bond

(c) C1 — N and C5 — N bonds are of same length but

longer than C3 — N bond

(d) C1 — N and C3 — N bonds are of different length

but both are longer than C5 — N bond

55. (A) Assertion : Tertiary carbocations are generally formed Ans. (a, b, c, d)
more easily than primary carbocations. Sol. Due to S.I.R. effect all the options are incorrect. Options
Reason : Hyperconjugation as well as inductive effect (a),(b),(c) and (d) are correct.
due to additional alkyl groups stabilize tertiary
carbocations.

(a) A (b) B 57. (M) Which statements among following are correct ?

(a) Hydration effect stabilise dimethyl ammonium ion

(c) C (d) D
more than trimethyl ammonium ion
Ans. (a)

Sol. Consider the examples.

(b) is more basic than

(c) nucleophilicity in DMSO

(d) Phenol is more acidic than CH3OH

Ans. (a, b, d)

Sol. Order of mudeophilicity should be

So, hyperconjugation is more in tertiary carbocation

due to more number of µ -H atoms. and +Ieffect. So, option c is incorrect.

Options (a), (b), and (d) are correct.

56. (M) Which of the statements are incorrect about the

 GOC 76

58. (A) Assertion : The C º C distance is longer than C = C the chain of carbon atoms.
distance

Reason : Both C atoms in alkenes are sp2 hybridized.

61. (A) Assertion : Conjugated dienes are more stable than non-
(a) A (b) B conjugated dienes.
(c) C (d) D Reason : 1,4-Pentadiene is a non-conjugated diene.
Ans. (d)
(a) A (b) B
Sol. (c) C (d) D

Ans. (b)

Sol. Conjugated dienes are more stable than non-conjugated

dienes because conjugated dienes are stabilized by
resonance.
59. (A) Assertion : Ethylene is more reactive than ethane.

Reason : Ethylene possess p bond.

(a) A (b) B
1,4-Pentadiene is a non-conjugated diene.
(c) C (d) D

Ans. (a) In conjugated dienes conjugation

Sol. Ethylene passess p-bond, which can behave as (p alternate p bond) must be present.

mudeophile due to p-electrons.

62. (A) Assertion : All carbon atoms in 1,3-butadiene are sp2
So, it is more reactive than ethane.
hybridized.
Option a is correct.
Reason : 1,3-Butadiene is a conjugated diene.

(a) A (b) B
60. (A) Assertion : The two structures, CH3 – CH2 – CH2 – C º
(c) C (d) D
CH and are chain isomers.
Ans. (b)

Reason : The chain isomers differ in the chain of carbon

atoms. Sol.
(a) A (b) B

(c) C (d) D All carbon atoms are SP2 hybridized. It is a conjugated

diene.
Ans. (a)
Option b is correct.

Sol.
63. (A) Assertion : CHCl = CHBr exhibits geometrical isomerism.
are chain isomers become the chain isomers differ in
 77 GOC

Reason : Presence of C = C is the condition for a

compound to exhibit geometrical isomerism.

(a) A (b) B

(c) C (d) D

Ans. (c)

Sol.

can show geometrical isomerism

a) There should be a frozen rotation about two adjacent

atoms in the molecule.

b) Both substituents on each carbon should be different

about which rotation is frozen.
 69 GOC

EXERCISE - 4 : PREVIOUS YEAR IIT QUESTIONS

Objective Questions (Only one correct option) 3. The compounds which gives the most stable carbonium
ion on dehydration is (1989)
1. The bond between carbon atom (1) and carbon atom (2) in
compound involves the (a)

hybridisation as
(1987)
2 2 3
(a) sp and sp (b) sp and sp
(c) sp and sp 2
(d) sp and sp (b)
Ans. (c)

Sol. N º C - CH = CH2 (c)

1 2
- -
sp sp2

(d)
2. Polarisation of electrons in acrolein may be written as Ans. (b)
(1988)

(a) Sol.

(30, most stable alkyl carbocation)

(b)
4. The number of sigma and pi-bonds in 1-butene-3-yne are
(1989)
(a) 5s and 5p (b) 7s and 3p
(c)
(c) 8s and 2p (d) 6s and 4p
Ans. (b)

(d)

Ans. (d) Sol.

5. Amongst the following, the most basic compounds is

(1990)
Sol.
(a) benzylamine (b) aniline
(c) acetanilide (d) p-nitroaniline
 GOC 70

Ans. (a) (a) III > IV > I > II (b) I > IV > III > II
(c) II > I > III > IV (d) IV > III > I > II
Ans. (d)
Sol.
Sol. Nitro group from para position exert electron withdrawing
resonance effect, increases acidity of phenol the most.
Lone pair is not involved in resonance, most basic. In all This followed by meta nitro phenol in which nitro group
other cases, long pair of nitrogen is involved in resonance, exert electron withdrawing effect on acidity. CH3 - is an
less basic.
electron donating group, decreases acid strength. Hence,
the overall order is
6. The hybridisation of carbon atoms in single bond
IV > III > I > II
is (1991)
(a) sp3 – sp3 (b) sp2 – sp3
9. Among the following compounds, the strongest acid is
(c) sp – sp3 (d) sp3 – sp
(1988)
Ans. (d)
(a) (b) C6H6
Sol. H - C º C - CH = CH2 (c) C2H6 (d) CH3OH
- -
sp sp2 Ans. (d)
Sol. Although alcohols are weaker acid than water, it is stronger
than ammonia and terminal alkynes.
7. What is the decreasing order of strength of the bases ?

OH - , NH -2 , H – C º C - and CH 3 - CH 2- 10. The most unlikely representation of resonance structures

of p-nitrophenoxide ion is (1999)
(a) CH 3 - CH 2- > NH 2- > H - C º C - > OH -

(b) H - C º C - > CH 3 - CH -2 > NH -2 > OH -

(c) OH - > NH -2 > H - C º C - > CH 3 - CH 2-

(d) NH -2 > H - C º C - > OH - > CH 3 - CH -2

(a) (b)
Ans. (a)
Sol. IV > III > I > II

CH3CH2- > NH2- > H - C º C - > OH-

8. In the following compounds :

(c) (d)

Ans. (b)

The order of acidity is : (1996)

 71 GOC

(c) 3 > 1 > 2 > 4 (d) 1 > 2 > 3 > 4

Ans. (b)
Sol.
Sol. I is most basic due to formation of resonance stabilized
conjugate acid.
Octet of nitrogen is violated.

11. Which of the following, has the most acidic hydrogen ?

(2000) Resonance stabilized conjugate acid
(a) 3-hexanone (b) 2, 4-hexanedione IV is amide, least basic.
(c) 2, 5-hexanedione (d) 2, 3-hexanedione
Ans. (b)

Sol. Methylene (- CH2 -) with carbonyl on both side is highly

acidic. -
Also among alkyl amines, 20 is more basic than 10 amine.
Hence, overall order of basic strength is

1> 3>2> 4

14. Which of the following hydrocarbons has the lowest dipole

12. Among the following, the strongest base is (2000) moment ? (2002)
(a) C6H5NH2 (b) p-NO2C6H4NH2 (a) cis-2-butene (b) 2-butyne
(c) m-NO2— C6H4NH2 (d) C6H5CH2NH2 (c) 1-butyne (d)
Ans. (d) Ans. (b)

Sol. CH3 - C º C - CH3

symmetric
Sol.

15. Identify the correct order of boiling points of the following

Lone pair is not taking part in resonance, most basic. In
compounds
other cases, long pair of nitrogen is part of delocalization
which decreases Lewis base strength. CH3CH2CH2CH2OH (1) CH3CH2CH2CHO (2)
CH3CH2CH2COOH (3) (2002)
(a) 1 > 2 > 3 (b) 3 > 1 > 2
13. The correct order of basicities of the following compounds
is (2001) (c) 1 > 3 > 2 (d) 3 > 2 > 1
Ans. (b)
Sol. Butanoic acid forms more exhaustive H-bonds than
butanol and butanal do not form intermolecular H-bonds.
Hence, boiling point order will be.
3>1>2
(a) 2 > 1 > 3 > 4 (b) 1 > 3 > 2 > 4
 GOC 72

16. Which of the following acids has the smallest dissociation

constant ? (2002)
(a) CH3CHFCOOH (b) FCH2CH2COOH
(c) BrCH2CH2COOH (d) CH3CHBrCOOH
Ans. (c)
(c)
Sol. Weakest acid BrCH2CH2COOH has smallest dissociation
constant.

17.

(d)

The product A will be

Ans. (a)
Sol. In general, the order of acid strength is
- C º CH < ROH < H2 O < PhOH < R - COOH
Therefore, during stepwise neutralisation of given acid,
(a) - COOH will be neutralized first.
In the second step, the phenolic - OH , assisted by - I
effect of - NO2 at meta position will be neutralized.

(b)
 73 GOC

18. Which of the following represents the given mode of

(d)
hybridisation sp 2 – sp 2 – sp – sp from left to right ?
(2003) Ans. (c)
(a) H2C = CH – C º N (b) HC º C – C º CH + -
Sol. H2C = CH - CH - CH - O - CH3
(c) H2C = C = C = CH2 (d) Long pair of oxygen is not the part of this mode of
delocalization.
Ans. (a)

H2C = CH- C º N 22. Which of the following is obtained when 4-methylbenzene

- - - - sulphonic acid is hydrolysed with excess of sodium
Sol.
sp2 sp2 sp sp
acetate ? (2005)

19. Among the following, the molecule with the highest (a)
dipole moment is (2003)
(a) CH3Cl (b) CH2Cl2
(c) CH2Cl2 (d) CCl4
(b)
Ans. (a)
Sol. CH3Cl has highest dipole moment.

(c)

20. (d)

Ans. (c)
Arrange in order of increasing acidic strength (2004)
Sol. A spontaneous neutralisation will occur between strong
(a) X > Z > Y (b) Z < X > Y acid and strong base as
(c) X > Y > Z (d) Z > X > Y
Ans. (a)
Sol. Carboxylic acid is stronger acid than ammonium ion, hence
- COOH(X) is most acidic. Z(NH3) is more acidic than
Y(NH3)due to -I effect of -COOH on Z. Hence, overall
acid strength order is X > Z > Y

21. Which of the following resonating structures of 1-methoxy-

1, 3-butadiene is least stable ? (2005)

(a)

(b)
23. When benzene sulphonic acid and p-nitrophenol are
(c) treated with NaHCO3, the gases respectively are (2006)
 GOC 74

(a) SO2, NO2 (b) SO2, NO

(c) SO2, CO2 (d) CO2, CO2
Ans. (d)

Sol.

25. The correct stability order for the following species is

(2008)

(a) (II) > (IV) > (I) > (III) (b) (I) > (II) > (III) > (IV)

(c) (II) > (I) > (IV) > (III) (d) (I) > (III) > (II) > (IV)
24. Among the following, the least stable resonance structure
Ans. (d)
is (2007)
Sol. The s - electron of C - H bond is delocalized with p-
(a) orbitals of p - bond.

(b)

(c) has no resonance stability but 20

(d) 2 0,

has resonance stability

Ans. (a)
Sol. The following structure has like charge on adjacent atoms,
therefore, least stable
 75 GOC

10, has no resonance stability

Therefore, overall stability order is : I > III > II > IV

Cl has overall electron withdrawing effect, increases acid

26. Hyperconjugation involves overlap of the following strength.
orbitals (2008)

(a) s-s (b) s-p

28. In the following carbocation ; H/CH3 that is most likely to
(c) p-p (d) p-p migrate to the positively charged carbon is (2009)
Ans. (b)

Sol.
(a) CH3 at C-4 (b) H at C-4

(c) CH3 at C-2 (d) H at C-2

Ans. (d)

Sol. H at C2 will migrate giving resonance stabilized carbocation.

27. The correct acidity order of the following is

(a) (III) > (IV) > (II) > (I) (b) (IV) > (III) > (I) > (II) 29. The correct stability order of the following resonance
structure is
(c) (III) > (II) > (I) > (IV) (d) (II) > (III) > (IV) > (I)

Ans. (a)

(2009)

Sol. (a) (I) > (II) > (IV) > (III) (b) (I) > (III) > (II) > (IV)
(c) (II) > (I) > (III) > (IV) (d) (III) > (I) > (IV) > (II)
Ans. (b)
 GOC 76

Sol. I is most stable because it has more covalent bonds and resonance effect, increases acid strength. Therefore,
negative charge on electronegative nitrogen. III is more phenol is less acidic than p-nitro phenol.
stable than II and IV due to greater number of covalent
On the order hand, methoxy group from para position,
bonds. Between II and IV, II is more stable since, it has
donate electrons by resonance effect, decreases acid
negative charge on electronegative atom and positive
strength of phenol. Also ethanol is weaker acid than
charge on electropositive atom. Hence, overall stability
phenol due to resonance stabilization in phenoxide ion.
order is I > III > II > IV
Hence,

30. Among the following compounds, the most acidic is

ethanol <p-methoxyphenol <phenol <p-nitrophenol <acetic acid

(2011)
(a) p-nitrophenol (b) p-hydroxybenzoic acid 32. The molecules that will have dipole moment are (1992)

(c) o-hydroxybenzoic, acid (d) p-toluic acid (a) 2, 2-dimethyl propane (b) trans 2-pentene

Ans. (c) (c) cis 3-hexene

Sol. A momo - substituted benzoic acid is stronger than a (d) 2, 2, 3, 3-tetramethyl butane
mono-substituted phenol as former being a carboxylic Ans. (b, c)
acid. among the given substituted benzoic acid, ortho -
hydroxy acid is strongest acid although -OH causes
electron donation by resonance effect which tends to
decrease acid strength.
Sol.
It is due to a very high stabilization of conjugate base by
intramolecular H-bond which outweigh the electron
donating resonance effect of -OH

The overall order of acid-strength of given four acids is

ortho-hydroxybenzoic acid

(pKa =2.98)>Toluic acid (pKa =4.37)>p-hydroxybenzoic acid

(pKa =4.58)>p-nitrophrnol(pK a =7.15)

Objective Questions (One or more than one correct option)

31. Phenol is less acidic than (1986)
(a) acetic acid (b) p-methoxy phenol
(c) p-nitrophenol (d) ethanol
33. The compound in which C uses its sp3-hybrid orbitals for
Ans. (a, c) bond formation is (2000)
Sol. Phenol is less acidic than a carboxylic acid (acetic acid). (a) HCOOH (b) (H2N)2 CO
Nitro group from para position exert electron withdrawing
(c) (CH3)3 COH (d) CH3CHO
 77 GOC

Ans. (c, d)
(a)

(b)
Sol.

(c)

(d)

Ans. (b, c)
Sol. In both (b) and (c), all the atoms are present in one single
plane

34. In the Newmann projection for 2,2-dimethylbutane

In (a) 1, 3- butandiene, conformational change is possible

between C2 - C3 bonds in which atoms will be present in
more than one single plane.

In (d) allene, the terminals H - C - H planes are

perpendicular to one another.
X and Y can respectively by (2010)
(a) H and H (b) H and C2H5
36. With respect to graphite and diamond, which of the
(c) C2H5 and H (d) CH3 and CH3
statements(s) given below is (are) correct ? (2012)
Ans. (b, d)
(a) Graphite is harder than diamond.
(b) Graphite has higher electrical conductivity than
diamond.

Sol. (c) Graphite has higher thermal conductivity than diamond.

(d) Graphite has higher C—C bond order than diamond.
Ans. (b, d)
On C2 - C3 axis, X = CH3 ,Y = CH3 Sol. Graphite has higher electrical conductivity because of
delocalization of electrical than in diamond.
On C1 - C2 axis, X = H,Y = C2H5
Graphite

2
35. Amongst the given options, the compounds(s) in which Carbon-Carbon bond order = 1 +
6
alll the atoms are in one plane in all the possible
conformations (if any), is (are) (2011) = 1.33
 GOC 78

Diamond Reason : o-hydroxybenzoic acid has intramolecular

hydrogen bonding.
Bond order = 1
Bond order of graphite is higher than diamond. (a) A (b) B

(c) C (d) D

ASSERTION – REASON Ans. (d)

In the following set of questions, two statements Sol. Statement I is incorrect; statement II is correct,
“Assertion” and “Reason” are given . Choose the correct intermolecular H-bonding in ortho-hydroxy benzoic acid
answer from the following options : lowers the boiling point.

(a) Assertion and Reason are true and the Reason is the correct
explanation of the Assertion.
Fill in the Blanks
(b) Assertion and Reason are true but the Reason is not a
39. Among the given cations, ............... is most stable.
correct explanation of the Assertion.
(sec-butyl carbonium ion, tert-butyl carbonium ion, n-butyl
(c) Assertion is true but the Reason is false.
carbonium ion) (1981)
(d) Assertion is false Reason is true.
Ans. Ter-butyl carbonium ion.
37. Asseration : p-nitrophenol is a stronger acid than
Sol. Tert-butyl carbonium ion because the three methyl group
o-nitrophenol.
stabilisers carbocation by +I effect.
Reason : Intramolecular hydrogen bonding make the
o-isomer weaker acid than p-isomer.
40. In acidic medium, ................ behaves as the strongest base.
(a) A (b) B
(nitrobenzene, aniline, phenol) (1981)
(c) C (d) D
Ans. Aniline
Ans. (a)
Sol. Aniline
Sol. Statement I is correct; statement II is correct, statement II
is the correct explanation of statement I.

Intermolecular H-bonding discourages release of H+= to 41. The compound having both sp and sp2 hybridised carbon
some extent, hence weaker acid than its para isomer. atoms is ............. (propane, propene, propadiene). (1981)

Ans. propene

Sol. Propene : CH2 - CH- CH3

- -
sp2 sp3

42. ............... ring is most strained. (cyclopropane, cyclobutane,

cyclopentane) (1981)

Ans. cyclopropane
38. Asseration : p-hydroxybenzoic acid has a lower boiling
point than o-hydroxybenzoic acid.
 79 GOC

Sol. Cyclopropane: here the C - C - C bond angle is 600 while methyl radical from methane. (1994)
the requirement is 1090.
Ans. Less

Sol. Less, stable free radical is formed.

43. The terminal carbon atom in butane is ............ hybridised.

(1985)
48. The IUPAC name of succinic acid is ............. (1990)
Ans. sp 3
Ans. Butanedioic acid
3
Sol. sp - hybridised

Sol.
44. A ................ diol has two hydroxyl groups on ............. carbon
atoms. (1985)

Ans. Germinal, same

Sol. Germinal, same 49. The kind of delocalisation involving sigma bond orbitals
is called ............... (1994)

Ans. hyperconjugation
45. The shape of (CH3)+ is ................. (1990)
Sol. hyperconjugation
Ans. Triangular planar

Sol. Triangular planar, carbon is sp2 - hybridised Subjective Questions

50. Arrange the following in the order of their increasing

basicity. p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline,
46. The structure of the enol form of CH3– CO – CH2– CO – CH3 aniline. (1985)
with intermolecular hydrogen bonding is ............ (1993)
Sol. p - nitroaniline < aniline < p - toluidine < N,
Ans. Cyclic
Sol. Cyclic
N - dimethyl - p - toluidine.

Nitro group, by electron withdrawing resonance effect

decreases the basic strength. Methyl group by electron
donating inductive effect, increases basic strength.

51. Although phenoxide ion has more number of resonating

structures than benzoate ion, benzoic acid is a stronger
acid than phenol. Why ? (1997)

Sol. In case of acetate ion, both the resonance structures are

47. The bond dissociation energy needed to form the benzyl
equivalent and negative charge always remains on
radical from toluene is ................. than the formation of the
electronegative oxygen. These factors makes acetate ion
 GOC 80

more stable than phenoxide ion in which negative charge 54. Give reasons for the following
also moves on carbon atoms.
is more basic than . (2000)

Sol. H - C º C - H is more acidic than CH2 - CH2

55. Match the following with their Ka values (2003)

Benzoic acid 4.2 × 10–5

p-nitrobenzoic acid 3.3 × 10–5

p-chlorobenzoic acid 6.4 × 10–5

p-methylbenzoic acid 36.2 × 10–5

p-methoxybenzoic acid 10.2 × 10–5

Sol. p-methoxy benzoic acid is the weakest and p-nitrobenzoic

52. Give reasons for the following in one or two sentences. acid is the strongest acid among these acids. Chloro group
has overall electron withdrawing effect on ring, therefore,
The central carbon-carbon bond in 1, 3-butadiene is shorter
increases acid strength of benzoic acid. Methyl group
than that of n-butane. (1998)
decreases acid strength of benzoic acid by + I effect.
Therefore,

Sol. Ka

p- methoxy benzoic acid 3.3 ´ 10-5

p-methyl benzoic acid 4.2 ´ 10-5

Benzoic acid 6.4 ´ 10-5

53. Discuss the hybridisation of carbon atoms in allene (C3H4) p-chlorobenzoic acid 10.2 ´ 10-5
and show the p-orbital overlaps. (1999)
p- nitrobenzoic acid 36.2 ´ 10-5

Sol.

56. Draw the resonating structures of .

(2003)
 81 GOC

Sol.

57. Which of the following is more acidic and why ?

(2004)

Sol. ;