GENERAL ORGANIC CHEMISTRY 1

EXERCISE - 1 : BASIC OBJECTIVE QUESTIONS

Introduction to Carbon and Its Compounds Because central carbon is sp3 - hybridized.
3. The hybridization of carbon atoms in C—C single bond of
1. In which of the following molecules, all atoms are coplanar?
H—C C — CH CH2 is :
(a) sp3 – sp3 (b) sp2 – sp3
(c) sp3 – sp (d) sp – sp2
(a) (b) Ans. (d)
Sol.

(c) (d)
4. Hybridized carbon atom used in the formation of the
compound CH3 — CH CH — CH2 — CH3 are :
(a) sp and sp3 (b) sp and sp2
Ans. (a)
(c) only sp (d) sp2 and sp3
Sol. In biphenyl, all the atoms are co-planar, because all the carbon Ans. (d)
atoms in biphenyl are sp2 hybridised.
2. In which of the following molecules, all atoms are not coplanar ? CH3 – C = C – CH2 – CH3
Sol. sp3 sp2 H H sp2 sp3 sp3

(a) sp3  4 bonds

sp 2  3 bonds

sp  2 bonds
(b)
5. In the hydrocarbon,

(c)
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
(d)
Ans. (d)
Sol.
Ans. (c)

Sol.
GENERAL ORGANIC CHEMISTRY 3

6. Which of the following statements is true about hybridization ? 9. In which of the following hybridization, bond angle is
(a) Hybrid orbitals frequently undergo linear overlaps making the highest ?
sigma bonds. (a) sp 3 (b) sp 2
(b) Hybrid orbitals frequently undergo lateral overlaps making (c) sp (d) sp3d
-bonds. In other words, there are several compounds in
which -bonds are formed using hybrid orbitals. Ans. (c)
(c) Hybrid orbitals are molecular orbitals. Sol. Bond angle will be highest in sp hybridization because
(d) A hybrid orbital bigger in size makes shorter bond. molecule will be linear (180°).

Ans. (a) 10.

Sol. 1. Hybrid orbital will form  bond. In this molecule (allene)
2. Unhybrid orbital will form  bond. (a) all three C-atoms are sp2-hybridized
7. (b) both terminal C-atoms are sp2-hybridized while central
C-atom is sp-hybridized
C1—C2 bond of this molecule is formed by (c) both terminal C-atoms are sp-hybridized while central C-
(a) sp –sp overlap
3 2
(b) sp –sp overlap
2 3 atom is sp2-hybridized
(c) sp–sp overlap
2
(d) sp2–sp2 overlap (d) none of these
Ans. (c) Ans. (b)

Sol. CH2 = C – C  N
3 2 1 Sol.

sp2 sp
(-bonds) (-bonds)
8. In which of the following compounds, C has used sp2 orbital Structural Representation of Organic Compounds
in making C—O bond ? 11. Underlined carbon is sp3 hybridised in
(a) (b)
(a) (b) (c) (d)
Ans. (b)
Sol. In Ethylamine, the underlined C is sp 3 hybridised as
(c) (d) shown in the diagram below -

H
Ans. (c)
|
OH OH CH 3  C  NH 2
|
Sol. sp
3
sp3 H
(4-bonds) (4-bonds)

Reacting Species
OH OH
12. Which of the following species is a nucleophile ?
sp2 sp3 (a) H2O (b) H3O
(3-bonds) (4-bonds)
(c) both (a) and (b) (d) none of these
Ans. (a)
GENERAL ORGANIC CHEMISTRY 3

Sol. H2O has an electron pair to donate. Hence, option (a) is Sol. Functional Group Suffix
correct. Alcohols -ol
13. Which of the following species is a nucleophile ? Aldehydes -al
Ketones -one
(a) CH3O (b) CH3OH
17. The correct decreasing order of priority for the functional
(c) both (a) and (b) (d) none of these groups of organic compounds in the IUPAC system of
Ans. (c) nomenclature is
(a) —COOH, —SO3H, —CONH2, — CHO
Sol. Both CH3O and CH3OH have electron pair to donate.
(b) —SO3H, —COOH, —CONH2, —CHO
Option (c) is correct.
(c) —CHO, —COOH, —SO3H, —CONH2
14. Which of the following species is an electrophile ?
(d) —CONH2, —CHO, — SO3H,—COOH
(a) H (b) H Ans. (a)
(c) both (a) and (b) (d) none of these Sol. The order of preference of functional groups is as follows
Ans. (a)
Sol. Electrophiles are electron deficient. They can carry Positive
charge.
Common Names of Organic Compounds
15. Which one of the following does not have sp2 hybridised
carbon ? 18. The IUPAC name of neopentane is
(a) Acetone (b) Acetic acid (a) 2-methylbutane (b) 2, 2-dimethylpropane
(c) Acetonitrile (d) Acetamide (c) 2-methylpropane (d) 2,2-dimethylbutane
Ans. (c)
Ans. (b)
Sol. Out of all the given compounds, acetonitrile does not
have a sp 2 hybridized carbon. So, the correct answer is Sol. IUPAC name of neopentane is 2,2-dimethylpropane.
option (c). CH 3
O O |
|| || H 3C  C  CH 3
CH 3  C  CH 3 CH 3  C  OH |
Acetic acid CH 3
acetone
19. The IUPAC name of CH3COCH (CH3)2 is
O
(a) isopropylmethyl ketone
|| CH 3  C  N (b) 2-methyl-3-butanone
CH 3  C  NH 2
Acetonitrile
Acetamide (c) 4-methylisopropyl ketone
(d) 3-methyl-2-butanone
IUPAC System of Nomenclature
Ans (d)
16. The suffixes for alcohols, aldehyes and ketones according
Sol. According to IUPAC Nomenclature, the name of the
to IUPAC system are respectively :
given molecule would be 3-methyl-2-butanone.
(a) -alc, -ald, -ket (b) -ol, -al, -ket
(c) -ol, -al, -one (d) -coh, -ald, -one
Ans. (c)
GENERAL ORGANIC CHEMISTRY 5

20. The correct IUPAC nomenclature for the following alcohol (a) 2, 5, 6-trimethylheptane
is : (b) 1,3-isopropyl-3-methylpropane
(c) 2, 6, 3-trimethylheptane
(d) 2,3,6-trimethylheptane
Ans. (d)
(a) 2-ethyl-2-butanol
Sol. Name the longest C chain using the Lowest Locants Rule.
(b) 3-methyl-3-pentanol
1 2 3 4 5 6 7
(c) 3-ethyl-3-methyl-3-pentanol
H 3C  CH  CH  CH 2  CH 2  CH  CH 3
(d) 1, 1-diethylanol | | |
Ans : (a) CH 3 CH 3 CH 3

Sol . The compound is an alcohol. Thus, its IUPAC name is So, according to IUPAC Nomenclature, the compound is
alkanol. Select the longest possible continuous C chain named as 2,3,6 - trimethylheptane.
carrying the -OH group: with lowest locant rule. 24. Name of the compound given below is :

21. The IUPAC name of the compound

(CH3)2 CH – CH = CH – CHOH – CH3 is : (a) 2,3-diethylheptane (b) 3-methyl-4-ethyloctane
(a) 5-methylhex-3-en-2-ol (c) 5-ethyl-6-methyloctane(d) 4-ethyl-3-methyloctane
Ans. (d)
(b) 2-methylhex-3-en-5-ol
Sol. According to longest chain rule and lowest locant rule
(c) 2-hydroxy-5-methyl-3-hexene
CH3
(d) 5-hydroxy-2-methyl-3-hexene
H3C 1 3 5 7
Ans. (a) 2 4 6 8
CH3
6 5 4 3 2 1
Sol. CH 3  CH  CH  CH  CH  CH 3 CH3
| | The IUPAC name of this compound is 4-ethyl-3-
methyloctane
CH 3 OH
5 methyl hex 3 en  2  ol
25. The IUPAC name of is
22. The IUPAC name of the compound

is (a) 1, 1-diethyl-2, 2-dimethylpentane

(b) 4, 4-dimethyl-5, 5-diethylpentane
(a) 3, 3-dimethyl-1-hydroxy cyclohexane (c) 5, 5-diethyl-4, 4-dimethylpentane
(b) 1, 1-dimethyl-3-hydroxy cyclohexane
(d) 3-ethyl-4, 4-dimethylheptane
(c) 3, 3-dimethyl-1-cyclohexanol
(d) 1, 1-dimethyl-3-cyclohexanol Ans. (d)
Ans. (c) Sol. According to IUPAC Nomenclature,
Sol. The IUPAC name of this compound is 3, 3-dimethyl-1- 6 2
cyclohexanol. 3
7 4 1
23. The IUPAC name of the following compound is : 5

3-ethyl-4, 4-dimethylheptane
GENERAL ORGANIC CHEMISTRY 5

26. The correct IUPAC name of the following compound : 29. The IUPAC name of CH3CH2C(Br) CHCl is :
(a) 4-chloro-3-bromo but-3-ene
is (b) 2-bromo-1-chloro butane
(c) 2-bromo-1-chloro but-1-ene
(a) 4 – methyl – 3 – ethylhexane
(b) 3 – ethyl – 4 – methylhexane (d) 2-bromo-2-ethyl-3-chloro propene
(c) 3, 4 – ethylmethylhexane Ans. (c)
(d) 4 – ethyl – 3 – methylhexane
Ans. (b) Sol.

2 4 6
3
1
Sol. 5
30. The IUPAC name of is :
3 – ethyl – 4 – methylhexane
27. The IUPAC name of CH3C(CH3)2 CH2CH CH2 is :
(a) 3-propylpent-1-ene (b) 3-ethylpent-1-ene
(a) 2,2-dimethyl-4-pentene
(c) 4-ethylhex-1-ene (d) 3-ethylhex-1-ene
(b) 4,4-dimethyl-1-pentene
Ans. (d)
(c) 1,1,1-trimethyl-3-butene
1 2 3
(d) 2-chloro-4,4-dimethylhexane Sol. H 2 C  CH  CH  CH 2CH 3
Ans. (b) |
CH 2  CH 2  CH 3
Sol. The longest continuous chain containing the functional 4 5 6
group that gives the functional group lowest possible 3  ethyl hex  1  ene
number. Numbering start from C = C, group.
31. The IUPAC name of CH3  C  CCH  CH3 2 is:
(a) 4-methyl-2-pentyne

(b) 4, 4 -dimethyl-2-pentyne
The IUPAC name of this compound is 4,4- dimethyl-1-
pentene (c) methyl isopropyl acetylene
28. The name of according to IUPAC (d) 4,4,4-trimethyl-1-butene

nomenclature system is : Ans. (b)

(a) 2,3-dibromo-1,4-dichlorobutene-2
(b) 1,4-dichloro-2,3-dibromobutene-2 Sol.
(c) dichlorobromobutene
(d) dichlorobromobutane
4, 4 -dimethyl-2-pentyne
Ans. (a)
32. The IUPAC name of is :
Sol. According to alphabetical order

(a) 2,2-diethyl pentanoic acid

(b) 2,4-dimethyl hexanoic acid
The IUPAC name of this compound is 2,3-dibromo-1,4- (c) 2-methyl-4-ethyl pentanoic acid
dichlorobutene-2
(d) 4-ethyl-2-methyl pentanoic acid
GENERAL ORGANIC CHEMISTRY 7

Ans. (b) Introduction of Reaction Intermediates

35. Due to the presence of an unpaired electron, free radicals
Sol. are
(a) cations (b) anions
(c) chemically inactive (d) chemically reactive
2-4-dimethyl hexanoic acid Ans. (d)
33. The IUPAC name of the compound Sol. Free radicals are highly reactive due to presence of an
unpaired electron. They readily try to pair-up the odd
electrons.
36. For the reactions
is :
(a) 3-ethyl-4-methylhex-5-en-2-ol
(I)
(b) 3-ethyl-4-ethylhex-1-en-5-ol
(c) 3-ethyl-2-hydroxy-4-methylhex-5-ene
(d) none of the above (II)
Ans. (a)
Sol. -OH functional group is preferred to double bond.

6 5 4 3 2 1 (III)
H 2 C  CH  CH  CH  CH  CH 3
| | |
CH 3 C2 H 5 OH (IV)
3 ethyl  4 methyl hex 5  en  2  ol

34. Which of the following compounds has incorrect IUPAC

nomenclature ? The correct decreasing order of enthalpies of reaction for
producing carbocation is

(a) (b) (a) H1o  H o2  H 3o  H o4

(b) H o4  H1o  H o2  H 3o

(c) (d) (c) H 3o  H 2o  H1o  H 4o

(d) H o2  H1o  H o4  H 3o
Ans. (b)
Ans. (d) Sol. Least stable carbocation formation will lead to highest
Sol. The carbon with -OH group has to be given least locant enthalpy of reaction, carbocation stablity order is
number. So the molecule would be named as 3- III > II > I > IV
methylbutan-2-ol and not 2-methyl-3-butanol. Hence, order of enthalpy of reaction

4 3 2 1 H 40  H10  H 20  H 30
CH 3  CH  CH  CH 3 37. The order of reactivity of the following alcohols towards
| | conc. HCl is :
CH 3 OH
3 methylbu tan  2  ol
GENERAL ORGANIC CHEMISTRY 7

(c)
(I) (II)
(d)
Ans. (a)
(III)
Sol. R or R – CH = CH2

Inductive Effect
(a) I > II > III (b) I > III > II
(c) III > II > I (d) III > I > II (3°C > 2°C > 1°C)

Ans. (d)
Sol. The reaction will involve the formation of carbocation. 40. Inductive effect of Cl atom operates in
Hence, alcohol forming more stable cation will be more (a)
reactive. Hence, carbocation are (b)
F +
(c)
(I)
CH3 CH3 (d) all of these
+ Ans. (d)
F
(II) + (III) Sol. The effect of the sigma electron displacement towards the
more electronegative atom by which one end becomes
Order follows,
III > I > II positively charged and the other end negatively charged is
known as the inductive effect.
Inductive Effect
41.
38. Inductive effect of —CH3 group operates in
Which of these groups has –I effect ?
(a) I (b) II
(a) (b) (c) III (d) all of these
Ans. (d)

Sol. –NO 2  Cl  I

(c) (d) all of these
N, Cl, I have tendency to attract electrons.Thus, they show
Ans. (d) -I effect.

Sol. Stability of carbocations will be decided on the basis of + I 42. Inductive effect of a —CH3 group operates
effect of -CH3 group. Inductive effect of the CH3 group
operates in all three molecules.
(a) (b)
39. In the following benzyl/allyl system

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

(R is alkyl group)
decreasing order of inductive effect is Ans. (d)
(a)
(b)
GENERAL ORGANIC CHEMISTRY 9

Sol. Option (d) is correct. (a) Electronic orbits of carbon atom are hybridised
(b) The bond is weaker than the bond
Inductive effect works when difference in E.N. is found.
(c) The anion, HCOO– has two resonating structures
Resonance (d) The anion is obtained by removal of a proton from
the acid molecule
43.
Ans. (c)
Sol. HCOO– has two equivalent resonating structures

Among these compounds, which one has shortest C—Cl

bond ?
(a) I (b) II
(c) III (d) IV
Ans. (a) 47.

Sol. In I, resonance can occur so partial double bond character Which of the following statements is true about this molecule ?
will be there. Hence, it will have shortest C-Cl bond length. (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
(d) C1—C2 and C2—C3 bonds are of same length
Ans. (b)
44. Heat of hydrogenation of cyclohexene is –28.6 kcal/mol and
that of benzene is –49.8 kcal/mol. Then resonance energy of Sol. C3-C4 double bond is in conjugation with both the double
benzene will be bonds on either side but C1-C2 in only in conjugation with
(a) 46 kcal/mol (b) 39 kcal/mol C3-C4. So, bond length of C3-C4 will be longer.
(c) 36 kcal/mol (d) 30 kcal/mol
48.
Ans. (c)

Sol.

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
Hth = 3× (-28.6) = - 85.8 Kcal/mol
Ans. (b)
Resonance Energy = - 49.8 - (-85.8) = 36.0 kcal / mol
Sol. In II octet of carbon is (C+) is incomplete in I, III octet is
45. Resonance structure of a molecules should have complete. So, II is least stable. In III negative charge is on
(a) Identical arrangement of atoms more electronegative atom. So, it will be most stable. So,
(b) Nearly the same energy content
correct order is III > I > II.
(c) The same number of paired electrons
(d) All the above
Ans. (d)
Sol. Resonance structure of a molecules should have Identical
arrangement of atoms, nearly the same energy content and
same number of paired electrons. So all given options are
correct.
46. In the anion, HCOO– the two carbon-oxygen bonds are
found to be of equal length. What is the reason for it ?
GENERAL ORGANIC CHEMISTRY 9

Ans. (c)
49.

Sol.

III is most stable because all atoms with Complete Octet.

II is stabilized by electron pair donation from Oxygen atom

I is least stable among the given.

Therefore Stability order is III  II  I

Most Stable is "III"

51.

Among these canonical structures of pyridine, the correct

order of stability is
(a) ( I = V) > (II = IV) > III
(b) (II = IV) > (I = V) > III
The stability order of these canonical structures is
(c) (I = V) > III > (II = IV)
(d) III > (II = IV) > (I = V) (a) I > II > III (b) III > I > II
Ans. (a) (c) I > III > II (d) II > III > I
Ans. (b)
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 Sol. II will be least stable, because octet of C is incomplete. III
order is.
will be more stable than I, because in III +ve charge is on N
(I = V) > (II = IV) > III which is less electronegative than O. So, correct order is
III > I > II.

50.

The most stable canonical structure among these is

(a) I (b) II

(c) III (d) all are equally stable

GENERAL ORGANIC CHEMISTRY 11

52. Which of the following is most stable ? Sol. Option (b) is correct.

NH 3 does not have vacant orbitals and cannot expand its
octet.
55. The most unlikely representation of resonance structure of
p–nitrophenoxide ion is :

(a) (b)

(a) I (b) II
(c) III (d) IV
Ans. (d)
Sol. In IV, octet of each atom is complete. Hence, Option (d) is (c) (d)
correct.
Resonance or Mesomeric Effect
53. Which one of the following substituents at para-position Ans. (c)
is most effective in stabilizing the phenoxide Sol. In option (c), N is pentavalent which is not possible.
Option (c) is correct.
ions ? Concept of Aromaticity
56. Number of  electrons present in naphthalene is

(a) –OCH3 (b) –CH2OH (a) 4 (b) 6

(c) –CH3 (d) –COCH3 (c) 10 (d) 14
Ans. (d) Ans. (c)
Sol. Phenoxide ion es electron density on ortho and para Sol. Structure of naphthalene is
position, so electron with drawing group stabilize phenoxide
ion.
54. In which of the following molecule the resonance effect is
not present ?
Above structure contains 5  bonds.

(a) (b) 1  2e  , 5  5  2  10e 

(c) (d)

Ans. (b)
GENERAL ORGANIC CHEMISTRY 11

Hyperconjugation 60.
57. Which of the following orbital diagrams represents the case
of hyperconjugation ?

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

resonance energy of these radicals ?
(a) (b)
(a) I > II > III (b) III > II > I
(c) III > I > II (d) II > III > I
Ans. (a)
Sol More number of alpha hydrogens more will be the no bond
resonance.
(c) both (a) and (b) (d) none of these
Less the stability, less the no-bond resonance energy. So,
Ans. (a) the correct order is I > II > III.
Sol. Option (a) is correct
The interaction between the electrons of p systems (multiple
bonds, C = C) and adjacent “ sigma bonds (single H-C bonds) 61.
of the substituent groups in organic compounds is called
hyperconjugation.
Which of the following orders is correct for no-bond-
resonance energy of these radicals ?
58.
(a) I > II > III (b) III > II > I
(c) I > III > II (d) II > I > III
How many hyperconjugable H-atoms does this molecule has ? Ans. (c)
(a) 0 (b) 2 Sol. Free radical stability  number of  hydrogen.
(c) 3 (d) 4
62. Which of the following represents the case of
Ans. (d)
hyperconjugation ?
Sol. 4 hyperconjugable H-atoms are present. Option (d) is correct.
(a) (b)
H H

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

H H
59. Hyperconjugation occurs in
Ans. (b)
(a) CH CH2 (b) CH CH CH3 Sol. Option (a) is resonance.
3 3
Option (c) is tautomerism
(c) CH CH2 CH2 (d) all of these Option (b) is hyperconjugation
3

Ans. (d)
Sol. (C–H), positive charge conjugation
All 3 molecules contain saturated alpha hydrogen atoms.
Hence, hyperconjugation occurs in all three of them
Option (d) is correct.
GENERAL ORGANIC CHEMISTRY 13

63. Hyperconjugation occurs in Applications of Electronic Effects

65. Among the following acids which has the lowest pKa
(a) (b) value?
(a) CH3CH2COOH (b) (CH3)2CH—COOH
(c) HCOOH (d) CH3COOH
(c) (d) All of these Ans. (c)

Ans. (d) Sol. Lowest pK a  More K a  More acidic

Sol. Option (d) is correct. All can show hyperconjugation.
Because all have alpha hydrogen atoms. As R increases, acidity decreases in carboxylic acid due to
increase in electron density on O-H bond (where R is length of
alkyl chain). So, HCOOH is more acidic and has least value of
pKa.
64.
66. In which of the following molecules, –NO2 group is not
coplanar with phenyl ring ?
Canonical structures due to hyperconjugation in this
molecule can be written as
(a) (b)

(a) (b)

(c) (d)

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

Ans. (a) Ans. (c)
Sol. Steric hindrance is the cause i.e., all the bulky and highly
Sol.
negative charge group (-I and –NO2 )are close to each other
so they will distort each other. It is called (SIR effect).

67.

Which of the following orders is correct for the stability of

these carbanions ?

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

(c) II > I > III (d) I  II  III

Ans. (a)
Sol. +I effect of alkyl group will decrease the stability of
carbanion. Hence correct order is I > II > III.
GENERAL ORGANIC CHEMISTRY 13

Ans. (b)
68.
Sol. Vinyl carbocations are least stable. Vinyl carbocation is
unstable because of its hybridization and presence of double
bonds.
71. What is the correct order of stability of the given cations:

Which of the following orders is correct for the stability of

these carbanions ?
(a) I > II > III (b) III > II > I
(c) II > III > I (d) II > I > III
Ans. (b)
Sol. III and II can show resonance. So I is least stable. In III,
negative chargs can delocalize on 4 positions, but in II it can
delocalize on only 2 positions.So, III is more stable than II.
Hence, correct order of stability is III > II > I.

69.
(I) (II) (III)
(a) III > II > IV > I (b) I > II > III > IV
Which of the following orders is correct for the stability of
these carbanions ? (c) III > I > II > IV (d) IV > II > III > I
Ans. (a)
(a) I > II > III (b) III > II > I
Sol. Electron releasing group will increase the stability of
(c) II > I > III (d) III > I > II carbocation and electron withdrawing will decrease the
Ans. (b) stability of carbocation.

Sol. Negative charge on more elctronegative carbon atom will

stabilize the carbanion. So, more the % s character more will
be the electronegativity.

So , correct order is III > II > I. Electron with Electron Electron

drawing releasing releasing
70. Which of the following carbocation is least stable ?
+M is stronger than Hyperconjugation and +I combined.
So, correct stability order is III > II > IV > I.
72. Which of the following statements is correct about methyl
(a) (b) CH CH2
group ?
(a) It stabilizes both carbocation and free radical equally
(b) it stabilizes a free radical more than a carbocation
(c) it stabilizes a carbocation more than a free radical
(c) CH 2 CH CH2 (d)
(d) none of these
Ans. (c)
GENERAL ORGANIC CHEMISTRY 15

Sol. A carbocation is deficient in two electrons, whereas a free

radical is only one electron deficient. Due to this stabilisation
effect works much more effectively in case of carbocation.
73. The order of stability of the following carbocations
  Sol.
CH 2  CH  C H 2 ;CH3  CH 2  C H 2 ;
 I  II 

Electron releasing groups will decrease the stability of the

carbanions. Mesomeric effect work only at -o and -p
positions. Hence, order is II > I > III.
76. The increasing order of stability of the following free
radicals is
(a) III > II > I (b) II > III > I    
(a)  CH 3  CH   CH 3  C   C6 H 5  CH   C 6 H 5  C
2 3 2 3
(c) I > II > III (d) III > I > II    
Ans. (d) (b)  C6 H 5  C   C 6 H 5  CH   CH 3  C   CH 3  CH
3 2 3 2
   
Sol. Greater the number of resonating structures a carbocation (c)  C6 H 5  CH   C6 H 5  C   CH 3  C   CH 3  CH
2 3 3 2
possess, greater is its stability.    
74. The correct order of increasing acid strength of the (d)  CH 3  CH   CH 3  C   C6 H 5  C   C 6 H 5  CH
2 3 3 2
compounds Ans. (a)
(A) CH3CO2H (B) MeOCH2CO2H Sol. Radical is stabilized by  hydrogen. More the number of
 -hydrogen, more will be hyperconjugation more will be
radical stabilization.
(C) CF3CO2H (D) is Resonance is also a good stabilizing factor and is given
preference than hyper conjugation. More phenyl ring
more will be the resonance
(a) B < D < A < C (b) D < A < C < B So option a is correct.
(c) D < A < B < C (d) A < D < C < B Structural Isomerism
Ans. (c) 77.

Sol. Electron withdrawing groups increase the acid strength and

electron donating groups decrease the acid strength. So,
we get the correct order of increasing acid strength as
CF3CO2H > MeOCH2CO2H > CH3CO2H > (Me)2CHCO2H.
So , the correct option is (c).

Among these, chain isomers are

75.
(a) I and II (b) I and III
(c) II and III (d) all of these
Which of the following orders is correct for the stability of Ans. (d)
these carbanions ? Sol. The molecular formula is the same for all but they differ in
(a) I > II > III (b) III > II > I carbon chain length.

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

Ans. (d)
GENERAL ORGANIC CHEMISTRY 15

78. Ans. (d)

Sol. II and III are positional isomers. I is functional isomer of II
and III.

81.

OH

Among these, I is the chain isomer of

(a) II only (b) III only Among these functional isomers are
(c) both (d) none of these (a) I and II (b) I and III
Ans. (a) (c) II and III (d) Both (a) and (c)
Sol. I is a chain isomer of II and position isomer of III. Ans. (d)
79. Sol. I and III are alcohols. II is ether.
82. 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

Among these III is the chain isomer of (c) same chemical properties and physical properties
(a) I only (b) II only (d) same physical properties but different chemical properties.
(c) both I and II (d) none of these
Ans. (a)
Ans. (c)
Sol. Isomers have same molecular formula but different physical
Sol. Number of carbon atoms in chain are different in all 3
structures. and/or chemical properties. Hence, option (a) is correct.

80.
83.

Among these, positional isomers are

(a) I and II (b) I and III
(c) II and III (d) all of these

Which among these are tautomers ? Ans. (d)

(a) I and II (b) I and III Sol. Methyl groups are at different positions with respect to
each other.
(c) II and III (d) None of these
GENERAL ORGANIC CHEMISTRY 17

84. The compound C4H10O can show Ans. (c)

(a) metamerism (b) positional isomerism Sol. Pent – 2 – ene can exhibit geometrical isomerism as each
(c) functional isomerism (d) all types doubly bonded carbon atom contains different groups.
Ans. (d)

Sol. C4H10O can represent an alcohol or an ether. Ether shows 88. The simplest alkene which is capable of exhibiting
geometrical isomerism has
metamerism, ether and alcohol shows positional isomerism,
and alcohol shows functional isomerism. (a) 3 carbon atoms (b) 5 carbon atoms
(c) 6 carbon atoms (d) 4 carbon atoms
85. The number of structural isomers for C6H14 is:
(a) 4 (b) 5 Ans. (d)

(c) 6 (d) 3 CH 3 CH3

Sol.
Ans. (b) But –2–ene
C C
Sol. The number of structural isomers for C6H14 is 5.
H H

89. 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)
Geometrical Isomerism
Sol. CH 3  CH  CH  CH 2  CH 2  CH 3
Hex  2  ene
86.
Hex-2-ene can exhibit geometrical isomerism because it
contains different groups around the double bonded
carbons.
90. Which one of the following compound will show geometrical
isomerism ?

(a) (b)

Which among these are stereo-isomers ? (c) (d)

(a) I and II (b) I and III
(c) II and III (d) all of these
Ans. (b)
Ans. (c)
Sol. In (a), (c) and (d) the similar atoms (groups) are on one
Sol. I and II are Positional Isomers carbon atom.
I and III are Positional Isomers Hence, they will not show geometrical isomerism. (b) has
II and III are Stereo Isomers different groups attached to double-bonded carbons. So, it
will show geometrical isomerism.
87. Geometrical isomerism will be exhibited by
(a) Pent–1–ene 91. Which of the following can exist as cis and trans isomers ?

(b) 3–Methylbut–1–ene (a) (b)

(c) Pent–2–ene (c) (d)

(d) All of these compounds
GENERAL ORGANIC CHEMISTRY 17

Ans. (c) 94. Which of the following compounds can show geometrical
Sol. Structures having similar atoms (or groups) on one or both isomerism ?
carbon atoms will not show geometrical isomerism. (a) Vinyl chloride (b) 1, 1–Dichloroethene
Hence,(a), (b) and (d) do not exist as cis trans isomers.
(c) 1, 2–Dichloroethene (d) Trichloroethene
Option (c) exists as cis trans isomer.
Ans. (c)
92. Which is a pair of geometrial isomers ?
Sol.

95. Which of the following pair of structures represent

geometrical isomers of each other?
(a) I and II (b) I and III

(c) II and IV (d) III and IV (a)

Ans. (c)

Sol. I will not show geomtrical isomerism. II and IV are geometrical

isomers. (b)
93. Which of the following will exhibit geometrical isomerism ?
(a) 1–Phenylbut–2–ene
(b) 3–Phenylbut–1–ene (c)
(c) 2–Phenylbut–1–ene
(d) 1, 1–Diphenylprop–1–ene
Ans. (a) (d)
Sol.
Ans. (c)

Sol. Only (c) will show geometrical isomerism.

As it has the same structural formula and double bonded

carbons have different groups attached.

Hence, option (c) is correct.