GENERAL ORGANIC CHEMISTRY 1

EXERCISE - 3 : ADVANCED OBJECTIVE QUESTIONS

Objective Questions I (Only one correct option] Ans. (a)

1. Which of the following alkenes will exhibit geometrical Sol. + I and + M effects decrease acidity of carboxylic acids. So,
isomerism ? option (a) is correct.

(a) CH3–CH2–CH2–CH = CH2 4. (I) CH3NH2 (II) (CH3)2NH (III) (CH3)3N

(b) CH3–CH2–CH = CH–CH3 Which of the following orders is correct for the basic-
strength of these 1º, 2º and 3º amines in gas phase ?
(c) CH3–CH2–CH = CH–CH2–CH3
(a) I > II > III (b) III > II > I
(d) both (b) and (c)
(c) II > I > III (d) II > III > I
Ans. (d)
Ans. (b)
Sol. Will not show geometrical isomerism
Sol Electron releasing groups increase the basic strength. Alkyl
groups exert +I effect. So the order of basic strength is
III > II > I. So option (b) is correct.

5. (I) CH3NH2 (II) (CH3)2NH

2. Aniline is weaker base than ethyl amine. This is due to
(III) (CH3)N
(a) – I effect of NH2 in aniline
Which of the following orders is correct for the basic-
(b) – R effect of NH2 in aniline strength of these amines in polar solvents (e.g., –H2O) ?
(c) + I effect of NH2 in aniline (a) I > II > III (b) III > II > I
(d) + R effect of NH2 in aniline (c) II > I > III (d) II > III > I
Ans. (d)
Ans. (c)
Sol. In aniline, L.P is involved in resonance so L.P will not be
available due to +R effect of –NH2 in aniline. So, option (d) is Sol. Order for basic strength is decided on the basis of
correct.
i ) Solvation
..
NH2
ii ) Inductive Effect

iii ) Steric Effect

So, correct option is (c).

Aniline
6.
3. Which of the following is strongest acid ?

(a) HCOOH (b) CH3COOH Which of these groups has –I effect ?

(a) I (b) II

(c) III (d) all of these

(c) (d) Ans. (d)

GENERAL ORGANIC CHEMISTRY 2

Sol : – F –COOOCH3 –COCl 9. Consider the following structures

I II III 

(I) CH 2  C H (II) CH 3  C H 2
All of these groups can exert -I effect. So, option (d) is
correct.  
(III) CH 2  CH  C H 2 (IV) C 6 H 5  C H  C 6 H 5
 CH3  CH  CH 2  C  CH
7. III The correct sequence of these carbocations in the
I II
decreasing order of their stability is
Which of these groups has +I effect ? (a) IV, III, II, I (b) I, II, III, IV
(a) I (b) II (c) IV, II, III, I (d) I, III, II,

(c) III (d) all of these Ans. (a)

Sol. I is least stable (Vinyl Carbocation). IV and III can show
Ans. (a) resonance but in IV positive charge can delocalize on 7
Sol. In II and III , C have sp2 and sp hybridization and so positions. So IV > III. But II can show hyperconjugation.
they exert -I effect due to electronegative carbon atom. So, correct order is IV > III > II > I .
Hence , option (a) is correct.
8. Which of the following alkyl benzenes has maximum
electron density?
10.

Which of the following no-bond-canonical structures is

(a) (b)
correct for this radical ?

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

Ans. (a)
Sol. More the number of conjugative α-H atoms more will
be the electron density. So option (a) is correct.

(c) (d) none of these

Ans. (a)
Sol. Alpha hydrogens involved in no bond resonance.
GENERAL ORGANIC CHEMISTRY 3

14. The reaction

11.

Regarrangement in this carbocation will produce represents

(a) nucleophilic substitution
(a)
(b) electrophilic addition
(c) electrophilic substitution
(b) (d) elimination reaction
Ans. (b)
(c) both (a) and (b) Sol. Addition of electrophile on double bond is taking place
(d) none of these which results in breaking of double bond. Hence, it is an
Ans. (a) electrophilic addition reaction.
Sol. Methyl shift will be done which will result in the formation 15. The hybridization of carbon in diamond, graphite and
of tertiary carbocation . acetylene are respectively:
12. The total number of contributing structures showing (a) sp3, sp, sp2
hyperconjugation (involving C–H bonds) for the (b) sp, sp2, sp3
following carbocation is: (c) sp3, sp2, sp
(d) sp2, sp3, sp
Ans. (c)
Sol. In diamond, each carbon combine with 4 other carbon
atoms with four sigma bonds. Hence, the hybridization of
carbon is sp3.
(a) 4 (b) 5
In graphite, each carbon combines with 3 other carbon
(c) 6 (d) 7 atoms with three sigma bonds. So, carbon is sp2
Ans. (c) hybridized.
In acetylene, one carbon combines with another carbon
Sol. The carbon next to carbocation is called alpha carbon
atom with three bonds (1 sigma and 2 pi bonds). So,
and hydrogen present on that carbon is alpha hydrogen.
carbon is sp hybridized.
There are 6 hyperconjugable H–atoms in this carbocation
The hybridization of carbon atom in diamond, graphite
which are contributing in the hyperconjugation.
and acetylene are respectively sp3, sp2, sp.
13. Which statement explains why the element carbon forms
16. CH2=CH–CH=CH–CH=CH–CH3
so many compounds with different shape?
How many geometrical isomers of this compound are
(a) Carbon atoms combine readily with oxygen. possible ?
(b) Carbon atoms have very high electronegativity. (a) 2 (b) 3
(c) Carbon readily forms ionic bonds with other carbon (c) 4 (d) 8
atoms. Ans. (c)
(d) Carbon readily forms covalent bonds with other Sol. First Double bond violates condition of geometrical
carbon atoms. isomerism whereas 2nd and 3rd double bond in above
Ans. (d) compound obeys conditions of Geometrical isomerism and
Sol. Carbon forms four covalent or shared bonds with other Hence shows 4 Geometrical isomers.
carbon atoms as well as many other kinds of atoms. It has
an almost limitless ability to bond with other carbon atoms
making possible a very large number of compounds.
GENERAL ORGANIC CHEMISTRY 4

17. CH3–CH2–CH=CH–CH=CH–CH3 20. Which is the major product of the following reaction ?
How many geometrical isomers of this compound are
possible ?
(a) 2 (b) 3
(c) 4 (d) 8
Ans. (c)

Sol. 22 = 4 geometrical isomers of CH3–CH2–CH=CH–CH= CH–

CH3 are possible.
18. Arrange following compounds in decreasing order of basicity. (a)

(b)

(a) IV > I > III > II (b) III > I > IV > II
(c) II > I > III > IV (d) I > II > III > IV
Ans. (d) (c)
Sol. In II L.P is not involved in resonance. In I, -I effect. In III
and IV resonance. In IV L.P. delocalization gains aromaticity.
So, option (d) is correct.

(d)
19.
Ans (b)

Sol. L.P. of N 1 will take part in resonance, but L.P. of N2 will be

more basic. Option b is correct.
III. CH3  NH 3

Which of the following orders is correct for the basic-

strength of these compounds ?

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

21. Correct order of basicity of various nitrogen in
(c) I > III > II (d) II > I > III
Ans. (c)
Sol. In aniline lone pair is involved in resonance. So, option c is
correct. Electron density is more at nitrogen.

(a) 1 > 2 > 3 (b) 2 > 1 > 3

(c) 2 > 3 > 1 (d) 3 > 2 > 1
GENERAL ORGANIC CHEMISTRY 5

Ans. (b)

(c) (d)
O
(3)
|| C2H5
(1) N Ans. (c)
C
H–N C2H5 Sol. In option (c), more conjugation is present.
Sol
N 25. Which of the following options is the correct order of relative
(2)
stabilities of cations as written below (most stable first) ?
CH3

N (3) is amide derivative least basic due to lone pair in

conjugation with oxygen atom, N(1) involved in resonance (I)
with benzene ring
N (2) is most basic due to no resonance as well electron
density increases due to the +I effect of alkyl groups. (II)

(III)
22.
(a) I > II > III (b) II > III > I
(c) III > I > II (d) I > III > II
Which of the following orders is correct for the basic- Ans. (a)
strength of these anilines ?
Sol. I can show resonance, II can show hyperconjugation,
(a) I > II > III (b) III > II > I III can show + I effect. So the correct order of stability is I >
II > III.
(c) II > I > III (d) I > III > II
26. What is the decreasing order of stability (most stable 
Ans. (d) least stable) of the following carbocations ?
Sol. Electron realeasing groups will increase the basic strength
in aniline. In -Cl, -I effect dominates. So correct order is I >
III > II. Option (d) is correct.
23. Which of the following is the most stabilized carbocation?

(a) (b)
(a) 3 >2 > 1 > 4 > 5 (b) 3 > 2 >5 > 4 >1
(c) 1  4  2  5  3 (d) 3  1  4  2  5
Ans. (b)
(c) (d) Sol :

Ans. (d)
Sol. In option (d), carbocation is stabilised by resonance effect
of OMe group.
24. Which carbocation is the most stabilized ?

(a) (b)
GENERAL ORGANIC CHEMISTRY 6

29. What is the decreasing order of strength of the bases ?

OH  , NH 2 , H – C  C  and CH 3  CH 2

(a) CH 3  CH 2  NH 2  H  C  C   OH 
So, correct order is 3 > 2 > 5 > 4 >1. Hence , option (b) is
correct.
(b) H  C  C   CH 3  CH 2  NH 2  OH 
27. Which of the following carbocation is most stable ?
(c) OH   NH 2  H  C  C   CH 3  CH 2

(a) (b) (d) NH 2  H  C  C   OH   CH 3  CH 2

Ans. (a)
Sol. Correct answer is option (a). The correct decreasing order
of strength of the bases is
(c) (d)
CH 3  CH 2  NH 2  H  C  C   OH  .
Ans. (c) Stronger the conjugate acid weaker will be the basic nature.
Sol. In option (c) conjugation is present. So, it will perform
resonance. Hence, option (c) is correct.
28. Relative stabilities of the following carbocation will be in
order : 30.

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. (d)
Sol. In II, carbanion is in conjugation with C=O, but in I, carbanion
competes with lone pair of O for resonance. Hence, the
(a) I < II < III < IV (b) IV < III < II < I
correct order is II > I > III. Option d is correct.
(c) IV < II < III < I (d) II < IV < III < I 31. Which of the following is least stable?
Ans. (c)
Sol. IV cannot show resonance but hyperconjugation, ethers
can show resonance, so IV will be least stable.

 M  H .C .
 
 I  I
Electron Electron
releasing releasing
(a) I (b) II
So correct order is I > III > II > IV. Hence, option c is correct.
(c) III (d) None
Ans. (b)
Sol. In I and III, Nitrogen holds negative charge in it’s 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.
GENERAL ORGANIC CHEMISTRY 7

32. Arrange the following in decreasing order of stability. 34. The three carbanions follows which order of stability

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

(c) II > I > III (d) II > III > I (a) I > II > III (b) I > III > II
Ans. (c) (c) II > I > III (d) II > III > I
Sol. Correct order is II > I > III .
Ans. (b)
Sol. Electron withdrawing groups increase the stability of the
carbanion. So, the correct order is I > III > II.

33. The correct order of stability of the three isomeric carbanions is:

35. The correct arrangement of the relative stability of the three

carbocation is :

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

(c) II > I > III (d) II > III > I
Ans. (d)
Sol. Correct order is II > III > I .

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

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

Ans. (d)

Sol. Electron withdrawing groups decrease the stability of

carbocation. -Cl can show only +M and -I effects. So, it in -
I - effect will depend upon distance from positive charge.
So, the correct order is III > I > II.
GENERAL ORGANIC CHEMISTRY 8

Hence, option (a) is correct.

38.

36. Which of the following is most likely to undergo a favourable

hydride shift ?

(a) (b)

(c) (d) Which of the following orders is correct for the stability of
these carbocations ?
Ans. (a) (a) I > II > III (b) III > II > I
Sol. Due to hydride shift in a 2o carbocation will convert into 3o (c) II > I > III (d) II > III > I
carbocation. Ans. (d)
37. Sol. Positive charge on bridged carbon is unstable. Thus, the
order of stability is II > III > I. Hence, option (d) is correct.

39. Rearrangement in this carbocation will

produce
(a)

Which of the following orders is correct for the stability of (b)

these carbocations ?
(c) both (a) and (b)
(a) I > II > III (b) III > II > I
(d) none of these
(c) II > III > I (d) III > I > II
Ans. (b)
Ans. (a)
Sol. Hydride shift is preffered to methyl shift. So, rearrangement
Sol. Correct order is
will form tertiary carbocation.
GENERAL ORGANIC CHEMISTRY 9

40. Which of the following is correctly named? Ans. (a)

Sol. In (b), (c) and (d), carbanion is stabilized by
resonance, but in (a) it is not stabilized. Moreover, in a
there is repulsion between lone of oxygen atom and
(a)
carbanion.
42. Which of the following ring compounds obeys Huckel’s
rule?
(a) C4 H 41 (b) C4 H 41
2
(c) C4 H 4 (d) C4 H 4
(b) Ans. (c)
Sol. Huckel’s rule (4n + 2 rule) : This rule define that in order
to be aromatic, a molecule should have a certain number
of  electrons within a closed loop of parallel adjacent

p-orbitals in this  4n  2   electrons where n = 0, 1, 2,

3 and so on.
(c) 2


Therefore in C 4 H 4 .  4n  2  6 e . Therefore Huckel’ss
rule is obeyed.
The structure of compound is

(d)
43. The correct acidity order of the following is

Ans. (a)
Sol.

(a) (III) > (IV) > (II) > (I) (b) (IV) > (III) > (I) > (II)
1-Chloro-2,4-dinitrobenzene
(Lowest locant = 1 + 2 + 4 = 7) (c) (III) > (II) > (I) > (IV) (d) (II) > (III) > (IV) > (I)
(Correct name) Ans. (c)
In 4-chloro-1,3-dinitrobenzene
(Highest locant = 4 + 1 + 3 = 8) Sol. Carboxylic acid is more acidic than the phenols. -I effect
(So incorrect) increases the acidic nature of phenol , while
hyperconjugation and +I effect decreases the acidic nature.
41. Which of the following is least stable?
44. How many open chain structural isomers of compound with
(a) (b) molecular formula C6H12 show geometrical isomerism?
(a) 2 (b) 3
(c) 4 (d) 5
Ans. (c)
(c) (d)
GENERAL ORGANIC CHEMISTRY 10

Sol. 47. Which of the statements are incorrect about the following
compound ?

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

Objection Question II
(b) C1 — N and C3 — N bonds are of same length but shorter
[One or more than one correct option]
than C5 — N bond
45. Br has low reactivity in CH 2  CH  Br because
(c) C1 — N and C5 — N bonds are of same length but
(a) the C  Br bond has a partial double bond longer than C3 — N bond
character (d) C1 — N and C3 — N bonds are of different length but
both are longer than C5 — N bond
(b) of the +M effect of bromine
Ans. (a, b, c, d)
(c) Br is electronegative
Sol. C1— N and C3— N bonds are of same length but
(d) None of the above
longer than C5—N bond due to SIR effect.
Ans. (a,b)
48. Which of the following alkenes are more stable than
Sol. In CH 2  CH  Br , resonance is observed due to which
partial double bond character will be there (+M effect of
bromine). So, bond will be strong. So option (a) and (b) will
be correct.

46. Which of the following have larger C—O bond length than

O
||
C—O bond length of CH 3  C  CH 3 ?
(a) (b)

(a) (b)

(c) (d)
(c) (d)

Ans. (a, c) Ans. (a, b, c, d)

Sol. In a, c options resonance can be observed due to Sol. Alkenes with more number of α-H atoms will be more stable.
conjugation. Hence partial bond character will be there
which will decrease the bond order and increase the bond 49. Which statements among following are correct ?
length. In option (b) no resonance with >C=O, because it (a) Hydration effect stabilize dimethyl ammonium ion more
will became anti aromatic. than trimethyl ammonium ion
GENERAL ORGANIC CHEMISTRY 11

Option c is correct.
(b) is more basic than 52. Asseration (A) : p-nitrophenol is a stronger acid than
o-nitrophenol.

(c) basicity order Reason (R) : Intramolecular hydrogen bonding make the
o-isomer weaker acid than p-isomer.
(d) Phenol is more acidic than CH3OH
(a) A (b) B
Ans. (a, b, d)
(c) C (d) D
Sol. Order of basicity should be
Ans. (a)

Sol. Intramolecular H-bonding in o-nitrophenol discourages

release of H+ to some extent, hence weaker acid than its
So, option (c) is incorrect. Options (a), (b) and (d) are correct. para isomer.
Assertion Reason
(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.
53. Assertion (A) : The acetate ion is a weaker base than the
(C) If Assertion is true but Reason is false. ethoxide ion.
(D) If Assertion is false but Reason is true.
Reason (R) : In carboxylic acids, the carbonyl group is
50. Assertion (A) : The C  C distance is longer than C = C polarized and so the carbon of the carbonyl group bears a
distance partial +ve charge.
Reason (R) : Both C atoms in alkenes are sp2 hybridized. (a) A (b) B
(c) C (d) D
(a) A (b) B
Ans. (b)
(c) C (d) D
Sol Acetate ion is resonance stabilized so, negative charge will
Ans. (d) participate in resonance. It will not be available for donation.
So, acetate ion is weaker base.
Sol. In C  C, both carbons are sp hybridized and C=C both
carbons are sp2 hybridized. So, C  C distance will be shorter O
||
than C=C. Acetate ion : CH3  C  O
51. Assertion (A) : Tropylium cation is more stable than
Ethoxide ion : CH 3  CH 3  O 
 CH3 3 C
54. Assertion (A) : The carbocation CF3 CH2 is less stable
Reason (R) : It is stabilized by both resonance effect and
inductive effect. than CF3 .

(a) A (b) B Reason (R) : In case of CF3 CH 2, CF3 is strong electron

(c) C (d) D withdrawing, therefore increases +ve charge whereas in

Ans. (c) CF3 , lone pair of ‘F’ overlap with vacant p-orbital of carbon
reducing +ve charge by p - p bonding or back bonding.
Sol. Tropylium cation is more stable than  CH 3 3 C  because (a) A (b) B
tropylium cation is aromatic in nature which is most stable. (c) C (d) D
So, assertion is true but reason is false.
GENERAL ORGANIC CHEMISTRY 12
Ans. (a)
(c) C (d) D
 
Sol. The carbocation CF3  CH 2 is less stable than C F3 Ans. (a)

because in C F3 conjugation of pi vacant orbital is present. Sol. Ethylene possess  bond, which can behave as a nucleophile
due to   electrons. So, it is more reactive than ethane.
So option a is correct. Option (a) is correct.
55. Assertion (A) : The two structures, 58. Assertion (A) : Conjugated dienes are more stable than non-
conjugated dienes.
CH3 – CH2 – CH2 – C  CH and CH 3  CH  C  CH are Reason (R) : 1,4-Pentadiene is a non-conjugated diene.
|
CH3 (a) A (b) B
chain isomers. (c) C (d) D
Ans. (b)
Reason (R) : The chain isomers differ in the chain of carbon
atoms. Sol Conjugated dienes are more stable than nonconjugated
dienes because conjugated dienes are stabilized by
(a) A (b) B resonance.
(c) C (d) D
CH 2  CH  CH  CH  CH 2
Ans. (a)
1,4-Pentadiene is a non-conjugated diene.
Sol. The given two structures are chain isomers because the 59. Assertion (A) : All carbon atoms in 1,3-butadiene are sp2
chain isomers differ in chain of carbon atoms. hybridized.
56. Assertion (A) : CHCl = CHBr exhibits geometrical isomerism. Reason (R) : 1,3-Butadiene is a conjugated diene.
Reason (R) : Presence of C = C is the condition for a (a) A (b) B
compound to exhibit geometrical isomerism. (c) C (d) D
(a) A (b) B Ans. (b)
(c) C (d) D
Sol. All the carbon atoms in 1,3 - butadiene are sp2 hybridized. It
Ans. (c)
is a conjugated diene.
Sol. CHCl = CHBr can show geometrical isomerism. 60. Assertion (A) : Tertiary carbocations are generally formed
more easily than primary carbocations.
Reason (R) : Hyperconjugation as well as inductive effect
due to additional alkyl groups stabilize tertiary carbocations.
(a) A (b) B
(c) C (d) D
Ans. (a)

Sol. Consider the examples,

Presence of C = C is the condition for a compound to exhibit CH 3

geometrical isomerism. |
H 3C  C  Tertiary carbocation
|
a) There should be a frozen rotation about two adjacent CH 3
atoms in the molecule.

b) Both substituents on each carbon should be different CH 3  C H 2 Primary carbocation
about which rotation is frozen.
So, hyperconjugation is more in tertiary carbocation due to
57. Assertion (A) : Ethylene is more reactive than ethane. more number of of α-H atoms and +I effect.
Reason (R) : Ethylene possess  bond.
(a) A (b) B
 GENERAL ORGANIC CHEMISTRY 13

Match the Following Paragraph Type Questions

Each question has two columns. Four options are Use the following passage, solve Q. 63 to Q. 65
given representing matching of elements from Passage
Column-I and Column- II. Only one of these four Hyperconjugation is no bond resonance. It involves 
options corresponds to a correct matching.For electrons of C—H bond. Greater the number of C — H bonds
each question, choose the option corresponding (-hydrogen atoms w.r.t. double bond) more will be
to the correct matching. hyperconjugative structures, more will be stability. Heat of
hydrogenation of alkenes are affected by hyperconjugative
61. Match the Column I and II (Matrix)
effects. Greater the hyperconjugative structures, lower will
Column-I Column-II be the heat of hydrogenation.
(A) — NO2 (P) –M effect
–
(B) — O (Q) +M effect
63. Which of the following has highest heat of hydrogenation?
(C) — O — CH3 (R) +I effect
(a) CH 2 CH 2 (b) But-l-ene
(D) C N (S) –I effect
(c) Isobutylene (d) Tetramethyl ethylene
Ans. (A – P, S; B – Q, R; C – Q, S; D – P, S)
Ans. (a)
Sol.  NO 2   M,  I  , O    M,  I  , Sol. Greater the number of hyperconjugative structures (or
OCH 3   M, I  greater α-H ’ s) lower will be the heat of hydrogenation.
C  N  M, I 
Option (a) has minimum α-H ’s, hence it is correct option.

62. Match the Column I and II (Matrix) 64. Which of the following has highest heat of combustion ?
Column-I Column-II (a) Isobutylene (b) But-l-ene
 (c) Tetramethyl ethylene (d) But-2-ene
(A) CH 3  C H  CH 3 (P) Pyramidal structure

Ans. (b)
(B) C H 3 (Q) Planar geometry
Sol. Alkene with minimum number of α-H wil l have highest heat

(C) CH 3  C H  CH 3 (R) Electrophile of combustion. But-1-ene has minimum number of α-H ’s, so it
(D) Singlet carbene (S) Nucleophile will have highest heat of combustion.
Ans. (A – Q, R; B – P, S; C – Q, R; D – Q, R) 65. Which of the following is incorrect hyperconjugative
structure?
Sol. Carbocation is sp hybridised & have trigonal planar
2

geometry.
Carbanion is sp3 hybridised & have pyramidal shape. Carbon
free radical is sp2 hybridised & have trigonal planar geometry.
Singlet carbene is sp2 hybridised & have trigonal planar
geometry (a) (b)
Carbocation, carbon free radical & singlet carbene are
electron deficient so behave as electrophile.
Carbanion is electron rich so behaves as a nucleophile.

(c) (d)
 GENERAL ORGANIC CHEMISTRY 14

Ans. (c) 67. Which of the following cations is hyperconjugation

destabilized?
Sol. In hyperconjugation hydrogen atom gets positive charge
and not negative charge.
(a) (b)
Use the following passage, solve Q. 66 and Q. 67
Passage
When (C—H)  electrons are in conjugation to pi bond, this
(c) (d)
conjugation is known as hyperconjugation : For any
compound to show hyperconjugation
2
(i) Compound should have one sp -hybridised carbon. Ans. (d)
2 3
(ii) -carbon with respect to sp should be sp
Sol. Absence of alpha- hydrogen & steric hindrance.
(iii) -carbon should contain at least one hydrogen atom.
No. of -carbon  stability of cation and alkene. Subjective Questions
66. Which of the following alkenes is most stabilized? 68. In acidic medium, ................ behaves as the strongest base.
(nitrobenzene, aniline, phenol)
(a) (b) Ans. Aniline will be more basic because NO2 will destabilised
the conjugate acid due to its electron withdrawing nature.

69. Arrange the following in the order of their increasing basicity.

(c) (d)
p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline, aniline.
Sol. p -nitroaniline < aniline < p - toluidine <N, N- dimethyl- p -
Ans. (c)
toluidine. Nitro group, by electron withdrawing resonance
Sol. More the number of H-C bonds attached to the unsaturated effect decreases the basic strength. Methyl group by
system more will be the probability of electron release by hyper electron donating inductive effect, increases basic strength.
conjugation. The compound C (2,3-dimethyl-2-butene) has 70. Give reasons for the following in one or two sen tences.
maximum number (12) of such H-C bonds attached to the The central carbon-carbon bond in 1, 3- butadiene is
unsaturated system. Hence, it will have a maximum extent of shorter than that of n-butane.
hyperconjugation and maximum stability. Sol. Buta-1-3-diene, i.e.,CH2=CH-CH=CH2 has sp2- sp2 (C-C) bond.
The s character is 33 . 3 % in 1,3-butadiene and 25.0 % in n-
butane. More is s-character in hybridization, lesser is bond
length.
Hence, the central carbon-carbon bond in 1,3- butadiene is
shorter than that of n-butane.