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FINAL TOUCH

REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED

BY
NAVNEET JETHWANI

GEOMETRICAL
OPTICS

ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

SINGLE CORRECT EXERCISE (GOC)

1. (A) (B) (C)

Compare carbon-carbon bond rotation across A, B and C

(A) A > B > C (B) B > C > A (C) B > A > C (D) B > C > A

Ans. (C)

*
KH *
2. A + H2 ; (C = C14)
H2O
Major product

Major products of the reaction is (are) :

*
*
(A) (B) (C) (D) All
*
Ans. (D)

3. Among the isomeric amine select the one with lowest boiling point.

H CH3 NH2
N
N
(A) (B) NHCH3 (C) (D)

CH3

Ans. (C)

4. Which of the following, is the product of the reaction between AlCl3 and CH3OCH3?

Cl Cl
– + CH3 + – CH3
(A) Cl—Al— O (B) Cl—Al— O
CH3 CH3
Cl Cl

Cl Cl
+ + CH3 – +
(C) Cl—Al— O (D) Cl—Al— CH3OCH3
CH3
Cl Cl
Ans. (A)

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5. In the following acid-base reaction, in which can backward reaction is favoured?

(A) EtO– + OH (B) KH + EtOH


O

(C) Me3CO–+ H2O (D) + CH3OH

Ans. (D)

6. Among the xylenes, which is thermodynamically most stable ?

(A) (B) (C) (D) All are equally stable

Ans. (B)

7. In sets a – d, only one of the set is incorrect regarding basic strength. Select it :

NH2

(A) Ph — NH — Ph1 < Ph — NH2 < (strong base)

H
N
(B) < <
N N
H

(C) < <


N N N
H H
NH2 NH2 NH2

(D) < <

NO2 CH3

Ans. (C)

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8. Which one of the following most stable ?

H Br H Br H Br Br
H H H H H H H H
(A) (B)
+
(C) (D) H
+
H + H H H H H H H
+
:NH2 :NH2 NH2 :NH2

Ans. (C)

9. Which of the following is not an appropriate resonance structure of the others

– – –
O O O O

(A) (B) (C) (D)


O O + O O
+ +

Ans. (D)

10. Identify benzene rign which has maximum e– density :

O O O
O
O
(A) (B) (C) (D)
O
O

Ans. (A)

11. Most basic isomer of compound C3H7N :

(A) CH3–CH2–CH=NH (B) CH3–CH=CH–NH2

(C) CH2=CH–CH2–NH2 (D) CH2=CH–NH–CH3

Ans. (C)

O O
+ +
NH NH +
12.
NH
A B C
Correct acidic strength :
(A) A > B > C (B) B > A > C (C) C > A > B (D) A > C > B

Ans. (D)

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13. Which will be least stable R.S. (least contributing) :


+ – – +
(A) CH2=CH– C H– C H–NH2 (B) C H2–CH=CH–CH= N H2
– + – +
(C) C H2– C H–CH=CH–NH2 (D) CH2=CH– C H–CH= N H2

Ans. (A)

14. For the molecule


a
HO b
OH

c
OH
The acidic strength order :
(A) Hc > Hb > Ha (B) Hb > Hc > Ha (C) Ha > Hb > Hc (D) Ha > Hc > Hb
Ans. (C)
15. In which case 2nd R.S. is more stable w.r.t. Ist R.S. :

+ O 2+ O
(A) CH3–N CH3–N
– –
O O
+
O + O
(B) CH2

+
(C) CH3–C–OCH3 CH3–C=OCH3
O –
O
+ – – +
(D) CH3–O=CH–CH–CH=CH2 CH3O–CH–CH–CH=CH2
Ans. (B)
16. Choose compound having highest pKb value :

NH
NH2 (a)
N
NH
NH2 (b)
N
NH
H2N (c)
N
(A) a (B) b (C) c (D) Both a & b

Ans. (C)

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17. Decreasing order :


p NH q r NH

O O
of marked bond length.

(A) p > q > r (B) q > p > r (C) r > q > p (D) p > r > q

Ans. (D)

18. Which of the following cations is most stable :

+
+
+
(A) (B) (C) (D) +
CH3 CH3 CH3 CH3

Ans. (D)

19. Consider the following reaction involving two acids shown below : formic acid and HF. Which of the following

statements about this reaction are true ?

(a) Formic acid is the strongest Bronsted acid in the reaction

(b) HF is the strongest Bronsted acid in the reaction

(c) KF is the strongest Bronsted base in the reaction

(d) KO2CH is the strongest Bronsted base in the reaction

(e) The equilibrium favours the reactants

(f) The equilibrium favours the products

(g) Formic acid has a weaker conjugate base

(h) HF has a weaker conjugate base

O O
+ – – +
KF + H OH H O K + HF
pKa = 3.8 pKa = 3.2

(A) a , b and f (B) b , d and h (C) a , c and h (D) b , d , e and h

Ans. (D)

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20. Use the following data to answer the question below :

H2
Ni H = –28.6 kcal mole–1

excess H2
(Ni) H = –116.2 kcal mole–1

Anthracene
Calculate the resonance energy of anthracene :

(A) 84 kcal / mol (B) 100 kcal / mol (C) 110 kcal / mol (D) 116 kcal / mol

Ans. (A)

21. Which is the major product of the following reaction ?

H
N
HCl Product
N H 1 mole

Cl H
H + H N
N H
(A) (B)
N+ Cl

N H H

Cl H H
N N Cl
(C) (D)
N H N H
Ans. (B)
22. Rank the following substance in order of decreasing heat of combustion (maximum  minimum) :

CH3 CH3 CH3

1 2 CH3 CH3
3 4
(A) 1 > 2 > 3 > 4 (B) 3 > 4 > 2 > 1 (C) 2 > 4 > 1 > 3 (D) 1 > 3 > 2 > 4

Ans. (C)

23. Which statement about the following equilirium is true ?

– + + –
O K + H2O OH + KOH
pKa = 15.7
t-butoxide pKa = 18

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(A) The equilibrium favours the product

(B) t-Butoxide is the dominant aionic species in the equilibrium

(C) Water is the weaker acid

(D) t-Butoxide is stabilized by resonance

Ans. (A)

24. For the following two acid base reactions, which statement is true ?
– –
(I) CH3CH2 + CH3NH2 CH3CH3 + CH3NH
pKa = 35 pKa = 50
– –
(II) F + H2O HF + HO
pKa = 15.7 pKa = 3.2
(A) It is favoured to the right, II is favoured to the left
(B) It is favoured to the lest, II is favoured to the right
(C) It is favoured to the right, II is favoured to the right
(D) It is favoured to the lest, II is favoured to the left
Ans. (A)

COOH HO
(Q)
25.

HO COOH HO COOH
(P) (R)

The correct acidic strength of acidic hydrogen P, Q and R is respectively :


(A) P > Q > R (B) P > R > Q (C) R > Q > P (D) Q > R > P
Ans. (A)

26. Compare relative stability of following resonating structure ?

– O O
O

(p) (q) (r)
CH3
C C C
N N N–

(A) p > q > r (B) q > p > r (C) q > r > p (D) p > r > q

Ans. (D)
27. The heat of hydrogenation of 1-hexene is 126 kJ mol. When a second double bond in introduced in the molecule, the heat of
hydrogenation of the resulting compound is found to be 230 kJ mol–1. The resulting compound (diene) is :
(A) 1,5-hexadiane (B) 1,4-hexadiane
(C) 1,3-hexadiane (D) Cannot predict from the given information
Ans. (C)

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28. Among the following compounds, the most basic compound is :

(A) (B) (C) (D)


N N O N
H H
Ans. (D)

29. Decreasing order of acidic strengths of following compounds is :


H CN

(x) (y) (z)

(A) x > y > z (B) y > x > z (C) z > y > x (D) z > x > y
Ans. (D)

H
(X)
N NH (Y)
30.
(Z)
O N O
H
The correct basicity order of atoms X, Y and Z is :

(A) X > Y > Z (B) Z > Y > X (C) Z > X > Y (D) Y > X > Z

Ans. (D)

31. Maximum number of Na metal equivalent used will be ?


OH

Na
HOOC C CH=CH2 (x eq.)

(A) 1 (B) 2 (C) 3 (D) 4

Ans. (C)

32. HO2C–CH=CH–OH, the direction of electron movement would be :

(A) toward –OH group

(B) neither –OH nor towards –CO2H

(C) toward –CO2H group

(D) At low temperature –OH group and at high temperature toward –CO2H group

Ans. (C)

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33. Polarisation of electron in acrolein (CH2-CH–CH=O) or R.H. can be written as :


+ – – +
(A) CH2 CH CH O (B) CH2 CH CH O

– – + +
(C) CH2 CH CH O (D) CH2 CH CH O
Ans. (A)

34. Consider following three halides :

(I) CH3–CH2–Cl (II) CH2=CH–Cl (III) C6H5Cl

Arrange C–Cl bond length of those compounds in decreasing order :

(A) I > II > III (B) I > III > II (C) III > II > I (D) II > III > I

Ans (A)

35. Gas liberated during reaction


COOH

NaHCO3

SO3H
14
(A) CO2 (B) SO2 (C) CO2 (D) SO3

Ans. (A)

36. Compound which is soluble in NaOH & NaHCO3 both :

OH OH CH3 OH
NO2
(A) (B) (C) (D)

NO2

Ans. (B)

37. Acidic strength order of given compound :

OH COOH OH COOH

NO2 CH3 (III) (IV)


(I) (II)

(A) I > IV > III > II (B) I > IV > II > III (C) IV > II > I > III (D) IV > I > II > III

Ans. (C)

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38. Which of the following is the correct order of basic nature.

(P) (Q) (R)


N N
N N
H
(A) Q > R > P (B) R > Q > P (C) R > P > Q (D) Q > P > R

Ans. (B)
39. Among the following compounds, the most acidic is :
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid

Ans. (C)

40. Decide decreasing order of bond length of C–Cl bond x,y and z in the following structure :
Cl
y
Cl
z

Cl x
(A) x > y > z (B) y > z > x (C) z > x > y (D) y > x > z
Ans. (D)
41. Imidaole has pKa = 7 with respect to its conjugate acid. Which N is protonated in this conjugate acid and why ?
3
N
Imidazole
1
N
H
(A) N1 becuase imidazole is an aromatic heterocycle where n = 1 as per Huckel’s rule.
(B) N1 is protonated because it is sp3 hybridised
(C) N3 is protonated because it is sp2 hybridised and has localised lone pair
(D) N1 is protonated because the lone pair is part of the aromatic pi system
Ans. (C)

42. In each of the following pairs of ions, which ion is more stable ?
+ + + +
(a) C6H5–CH2 and CH 2=CH–CH2 (b) CH3–CH2 and CH 2=CH
(I) (II) (I) (II)

+ +
CH2 CH2 CH3–CH–CH3 CH 3–N–CH3
(c) and (d) and
CH3–C–CH3 CH 3–C–CH3
+ +
(I) (II) (II)
(I)
(A) a–I , b–I , c–II , d–II (B) a–II , b–II , c–II , d–II

(C) a–I , b–I , c–I , d–I (D) a–II , b–II , c–I , d–I

Ans. (A)

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43. Which of the following two carbonium ions is more stable ? Explain why.

:
NH2
(a) + + (b) + +

(I) (II) (I) (I)


(A) a–II , b–II (B) a–I , b–I (C) a–I , b–II (D) a–II , b–I
Ans. (A)
44. Which of the most stable arenium carbocation ?
CH3 CH3 CH3 CH3
NO2
+
(A) H (B) (C) (D) H
+ +
+ NO
H NO2 H NO2 2

Ans. (C)
45. Which of the following compounds are aromatic compounds ?
H H
N N O S
(I) (II) (III) (IV)
N

H
O S N
N
(V) (VI) (VII) (VIII)
N N
N H
H H O OH
N N N
(IX) (X) (XI) (XII)
N N
O OH
(A) I , II , III , IV , V , VI , VIII , X , XII (B) I , II , III , VI , VIII , X , XI , XII

(C) I , II , III , IV , V , VI , VII , X, XII (D) I , II , III , V , VII , VIII , IX , X , XII

Ans. (C)

46. A compound shows a large dipole moment. Which of the following resonance structures can be

used to adequately explain this observation ?



+ – – +
(i) (ii) (iii) (iv)
+
(A) i (B) iii and iv (C) ii and iii (D) iv only

Ans. (B)

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47. Which of the following is not a resonance structure of the others ?



O O O O
– –
(A) (B) (C) (D)

Ans. (D)

48. Identify correct acidic strength order in the following compounds :

(i)
HO O

(ii) (iii)
HO OH

(A) ii > i > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (A)

49. The acidity of the protons H in each of the following is :

+ +
NMe3 PMe3 CH3
H H H

(i) (ii) (iii)

(A) i > ii > iii (B) ii > iii > i (C) ii > i > iii (D) iii > i > ii

Ans. (C)

50. Identify correct acidic strength order in the following compounds :

H H H

(i) (ii) (iii)

(A) iii > ii > i (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (A)

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51. Identify correct stability order in the following compounds :

+ + +
C CH CH
OO O O O O
(i) (ii) (iii)

(A) i > ii > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (B)

52. Which nitrogen in LSD is most basic ?

O
(3)
(1)
C–N(C2H5)2
HN
(2)
N
CH3

(A) 1 (B) 2 (C) 3 (D) All are equally basic

Ans. (B)

53. The decreasing order of basic strength is :

(5)
H2N (4)
NH
:

(1) N (3)
:N
:

H2N N (2)
CH3

(A) 1 > 5 > 3 > 4 > 2 (B) 4 > 1 > 5 > 3 > 2 (C) 5 > 4 > 1 > 2 > 3 (D) 4 > 5 > 3 > 1 > 2

Ans. (B)

54. Which of the following acid gives evolution of CO2 with NaHCO3 ?

OH HO O
NO2 COOH
(I) HCl (II) (III) (IV)
COOH
HO O
NO2

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COOH

(V)

COOH

(A) I , III , IV , V (B) III , IV , V (C) I , II , III , IV , V (D) I , III , IV

Ans. (C)

55. Maximum resonance energy is known for :

(A) (B) (C) (D)

Ans. (D)
56. Which of the following is most basic ?

N N
N N N
N N
(A) (B) (C) (D)
N

Ans. (C)
57. Which of the following is the most stabilised carbocation ?

OMe OMe OMe OMe


+
(A) (B) (C) + (D) +
+

Ans. (D)

58. The most stable canonical structure of the given molecule is :


– –
O O+ O + O
– +
(A) (B) (C) (D)

Ans. (B)

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59. Which is the least likely protonation site in the conjugated alkene shown below ?

(c)

(d) (a)

(b)

(A) a (B) b (C) c (D) d

Ans. (C)

60. Choose those that are resonance structures of protonated methyl vinyl ketone :

+ H
H :O
C C
H C CH3
H
Protonated methyl
vinyl ketone

H H H
:

:
:

H :O H :O H :O
+C C
(1) C C (2) (3) C + CH
H C + CH3 H C CH3 H C CH3
H H H

(A) 1 (B) 2 (C) 3 (D) 1 & 2

Ans. (D)
61. Which one of the following is the most basic compound :
(A) C6H5 – NH2 (B) C6H5 – NHCH3 (C) C6H5–N(CH3)2 (D) C6H5N(C2H5)2
Ans. (D)
62. Which of the following resonating structure is not possible for 2, 4, 6-trinitroiodo benzene

 
I  I I
I
O2N NO2 + O O2N NO2 O2N NO2
O2N N
O

  
N N N
NO2
O O O O O O
(I) (II) (III) (IV)

(A) I (B) II (C) III (D) IV


Ans. (B)

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63. Consider the following compound


O OH

OH O
CH3 –C–COOH
COOH III
O OH II
I
Which of the above compounds reacts with NaHCO3 giving CO2

(A) I, II and III (B) I and III (C) II and III (D) I and II

Ans. (A)

64. Which of the following is most acidic :


COOH COOH
COOH COOH

(A) (B) (C) (D)


CH3 NO2 CH3

Ans. (B)

65. Arrange marked atom in decreasing order of acidic strength

2
H O
3 1
H N H

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 2 > 3 > 1
Ans. (C)

66. Correct decreasing order of basic strength -

NH2
NH2 NMe2
N
N H N N
N H N
H
(II) (III)
(I)

(A) III > II > I (B) II > I > III (C) I > II > III (D) III > I > II

Ans. (A)

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67. Basicity order of N in following compound is :

O CH3 b CH3
N
H 2N C CH2 CH2 NH C CH3
c
NH
a

CH3 N
d
CH3

(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
Ans. (B)
68. Which of the following is the correct order of acidic strength.

COOH OH OH
NO2
(A) > > H2CO3 >

NO2

COOH OH OH
NO2
(B) > > > H2CO3

NO2

COOH OH OH
NO2
(C) > H2CO3 > >

NO2

(D) None

Ans. (A)

1 1 1
2 2 2
69. 3 3 3
4 4 4

These are three canonical structures of naphthalene. Examine them and find correct statement among the following:
(A) All C–C bonds are of same length (B) C1–C2 bond is shorter than C2–C3 bond
(C) C1–C2 bond is longer than C2–C3 bond (D) None
Ans. (B)

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NMe2 NH2 SO3H NO2 Br

70.

A B C D E

Steric inhibition of resonance takes place :


(A) In A, B only (B) In A, B, C, E (C) C only (D) In A only
Ans. (D)
71. Consider the following two structures and choose the correct statements -

O +
O O O
+
N N

(I) (II)

(A) Carbon-nitrogen bond length structure I is greater than that in structure II


(B) Carbon-nitrogen bond length structure I is less than in structure II
(C) Carbon-nitrogen bond length in both structure is same.
(D) It can not be compared.
Ans. (B)
72. Which of the following statements would be true about this compound :

NO2
5

1 3
NO2 NO2
Br

(A) All three C–N bonds are of same length.


(B) Cl–N and C3–N bonds are same length but shorter than C5-N bond.
(C) Cl–N and C3–N bonds are same length but longer than C5-N bond.
(D) Cl–N and C3–N bonds are of different length but are longer than C5-N bond.
Ans. (C)
73. Cyclopentadienyl anion is much more stable than allyl anion because
(A) Cyclic anion is more stabel than acyclic anion
(B) Delocalised anion is more stable than localised anion
(C) Cyclopentadienyl anion is aromatic in nature
(D) None of these
Ans. (C)

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74. Examine the following two structures for pyrrole and choose the correct statement given below
+

N N
H H
(I) (II)
(A) II is not an acceptable resonating structure because carbonium ions is less able than nitride ion.
(B) II is not an acceptable resonating structure because there is charge separation.
(C) II is not an acceptable resonating structure because nitrogen has ten valance electrons
(D) II is an acceptable resonating structure
Ans. (C)

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MULTIPLE CHOICE EXERCISE


1. Which of the following represents R.S. of biphenyl ?

+
(A) (B) – +

(C) (D)

Ans. (B,C,D)

2. What is the correct resonance hybrid of following molecules ?

+ + + –
(A) H2N C NH2 (Urea) (B) CH2 CH C CH (Vinyl acetylene)

O


O + –
(C) CH3—N (Nitro methane) (D) CH2 CH Cl (Vinyl chloride)

O
Ans. (A,B)

3. Which of the following option is incorrect ?

(A) PhN2+ is more stable w.r.t. RN2+ because in PhN2+ +ve charge undergoes delocalisation in ring
– –
CH2 CH2

(B) is more stable than

F Cl
(C) In PhSO3H, m position is relatively highly e– dense w.r.t. o/p position
(D) The e– movement with following compound HO–CH=CH–CO2H is towards –CO2H group
Ans. (A,B)

O O
4. Dianion of squaric acid

O O–
(A) 4-identical resonating structure (B) C–C bond lengths are identical
(C) C–O bond length = C–C bond length (D) Antiaromatic in nature
Ans. (A,B)

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5. Circle represent most acidic hydrogens in these molecules. Which of the following is correct representation

OH O
O
MeO2C
OH SH
(A) (B) (C) (D) None of these
HO
CF3 CO2H F

Ans. (A,B,C)

6. In the following acid base reaction, in which can forward reaction if favoured ?


(A) EtO + OH (B) KH + EtOH

O–

(C) – (D)
Me3CO + H2O + CH3OH

Ans. (A,B,C)

7. Which of the following is/are planar molecule ?


(A) H2C = C = CH2 (B) H2C=C=C=CH2 (C) H2C=C=O (D) NC–HC=CH–CN
Ans. (B,C,D)

8. Select the correct option(s) among the following :

(A) Correct acidity order is CF3–CH2–OH > CCl3–CH2–OH > CH3–CH2–OH

(B) Correct basicity order is CH3–CH2–NH2 > CH3–CH=NH > CH3–CN

(C) Correct acidity order is CH3–CH–CH2–OH > CH3–CH–CH2–OH > CH3–CH–CH2–OH

Me NO2 + NMe3

(D) Correct acidity order is HCCH > CH2=CH2 > CH3–CH3

Ans. (A,B,D)

SO3Na

9. Which will give HaOOC–CH2 C ONa as a product ? (Assume that ions were not present in

ONa

reactant)

(A) NaNH2 (B) Na (C) NaHCO3 (D) NaH

Ans. (A,B,D)

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10. Correct statement(s) is/are regarding given compound :

N N

N N
(I) H (II) (III) H
(A) Basic strength order I > II > III

(B) Acidic strength order I > II > III

(C) III compound having all inductive, mesomeric & hyperconjugation effects

(D) All I , II and III are heterocyclic compounds

Ans. (A,B,C,D)

11. Which of the following option(s) has correct direction of dipole moment ?

(A) (B) (C) CH–CH3 (D)

Ans. (B,C,D)

12. Identify the binary mixture(s) that can not be separated into the individual compounds, by differential extraction,

as shown in the given scheme :

NaOH (aq.)
Compoud-1 + Compoud-2
Binary mixture containing
compound 1 and compound 2
NaHCO3(aq.)
Compoud-2 + Compoud-2

OH OH CH2–OH OH
O2N NO2
(A) , (B) ,

NO2 SO3H

OH CH2–OH OH CH2–OH
NO2
(C) , (D) ,

COOH
Ans. (A,B,C)

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13. In which of the following compound(s) hyperconjugation effect is present :

(A) (B) (C) CH3–CH=CH3 (D)

CH2

Ans. (B,C,D)

14. Hydrogen bonding is primarily responsible for which of the following observation :

(A) p-nitrophenol is more acidic than o-nitrophenol

(B) Dimethyl amine is more basic than trimethyl amine in aqueous medium

(C) Boiling point of salicyladehyde is less than p-hydroxy benzaldehyde

(D) Benzoic acid is more acidic than phenol

Ans. (A,B,C)

15. In which of the following reaction product is/are aromatic ?


OH Br
+
H Ph–Li AgNO3
(A) (B) (C) (D) None of these

Ans. (A,B,C)

16. Select the incorrect statement(s) :

NH2 NH2
CH3
(A) is more basic than

COOH COOH
CH3
(B) is less acidic than

NMe2 NMe2
CH3
(C) is more basic than

NO2 NO2
CH3
(D) has shorter C–N bond length than

Ans. (A,B,D)

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17. Correct order of bond length of (C—O) bond :

H
O O O–H
p s
u
t
–O q r
O
O
(A) s > p > t (B) u > q > r (C) p = q (D) p > t > r

Ans. (A,B,C,D)

O
18. Compound(s) having higher bond rotation energy barrier across C = C than compound is/are :
O
O
O
(A)
O O (B)

O
O
(C) (D) O
O
Ans. (A,B,C,D)

19. Which of the following options are correct :

(A) p-chloro phenol is more acidic than p-fluoro phenol


O O
(B) Squaric acid dianion have identical R.S.

O O–
(C) Squaric acid dianion have all C–O bonds identical

(D) Squaric acid dianion have all C–C bond identical

Ans. (A,B,C,D)

20. Incorrect stability order is/are :

O + +
(A) O > + (B) >
+
O
+
(C) > (D) >
+
+ N + N
H H
Ans. (B,C)

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21. Which of the following is / are aromatic species :

(A) N (B) + (C) (D)


H O

Ans. (A,B,C)

22. Which of the following are incorrect :

(A) Order of heat of hydrogenation C–C=C–C–C–C=C–C < C–C–C=C–C=C–C–C

(B) Order of heat of combustion > > >

+
+
(C) Order of stability of carbocation > >
N +
N
H

(D) Order of heat of combustion is >


Ans. (A,B,C, D)
23. Select true statement(s) :

(A) Resonance effects bond length

(B) Inductive effect is a permanent effect.

O
COH
(C) In H2C most acidic H is connected directly to oxygen not on carbon.
COH
O
(D) In urea both C–N bond length are identical

Ans. (A,B,C,D)

24. Which has non-zero dipole moment ?

(A) (B)

(C) (D) HO OH

Ans. (A,B,C,D)

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25. Identify the correct order of dipole moment :

O O O
O
>
(A) > Ph Ph (B)
Ph Ph

(C) < (D) >

Ans. (A,B,D)

26. From the compound shown below, choose which is aromatic :

+ – –
O
(A) (B) (C) (D)
B
H
Ans. (A,B,C,D)
27. Identify the feasible reactions

COOH COONa

(A) + NaHCO3  + H2O + CO2

NH2 NHNa

(B) + NaHCO3  + H2O + CO2

OH ONa

(C) + NaHCO3  + H2O + CO2

COONa COOH COOH COO–

(D) +  +

NO2 NO2

Ans. (A, D)
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28. Select the number of compounds in which deprotonation gives aromatic anion :

O
HO CH2 O O
HN NH
O O
H
(A) (B) HO (C) (D)
O O
N O
Barbituric acid OH OH
Ascorbic acid H
(Vitamin - C)

Ans. (A, B, C, D)
29. Select correct statement :
(A) Carbon-oxygen bonds are equal length in acetate ion
(B) Resonating structures of acetate ion are equivalent
(C) Carbon-oxygen bonds are of unequal length in formate ion
(D) Resonating structures of formate ion are equivalent
Ans. (A, B, D)

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MISCELLANEOUS EXERCISE
Integer Type Questions
O
NaHCO3
1. Ph — C — O — H   (A) gas

Na
Ph — C CH   (B) gas

NaNH 2
Ph — OH   (C) gas

NaH
R — O — H   (D) gas
Sum of molecular mass of gas A + B + C + D is :

2. Analyse the following hydrogenation reactions and calculate resonance energy of ‘X’ in kcal/mole :

+ 2H2 H = – 58 kcal/mole

+ 5H2
H = – 94 kcal/mole
'X'
3. How many products will be aromatic ion when AgNO3 reacts with the following compounds ?

O
(a) Cl (b) Cl (c) (d)

Cl Cl
Cl
(e) CH2–Cl (f) CH2–Cl (g) (h) H–CC–Cl

4. How many compounds are soluble in aqueous NaHCO3 ?

OH OH COOH OH
H3C CH3 H3C
(a) (b) (c) (d)

+
– N CH3
O O

COOH O OH
HO OH HO O
(e) (f) (g) (h) H–CC–Cl
HO O N
O

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5. How many compounds are soluble in aqueous NaOH ?

COOH OH
HO OH
H3C
(a) (b) (c) (d)
HO O
CH3


O O OH
OH
COOH N+ N+ OH

HO OH O O
(e) (f) (g) (h)
+ N
– N CN
O O

6. How many compounds liberate hydrogen gas on reaction with Na metal ?

OH
OH
COOH
O
OH (c) H3C CH3
(a) (b) (d)
OH OH CH3

COOH O OH
HO OH O O
(e) (f) CH4 (g) (h)

OH OH
Cl

7.

X Y

Number of benzonoid ring in the following structures are X & Y :


Find out the value of (X + Y)

8. How many compounds liberate H2 gas on reaction with Na metal ?

OH OH OH
COOH
(i) (ii) (iii) (iv)

NO2

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O
O
(v) H–CC–H (vi) O (vii) (viii) CH2=CH2

HO
OH

(ix)

9. How many following compounds are more acidic than water ?

(a) SO3H (b) HCl (c) CH3 – C  CH (d) CO 2H

OH

OH
(e) (f) (g) (h) (i) NaOH
NO2

10. The structure of saccharin is given as follows :

O
C
NH
[Provided N is the donor atom in all cases]
S
O O

How many following compounds are more basic than saccharin ?

(i) CH3 C NH2 (ii) H 2N C NH2 (iii) CH3 C NH2


NH NH O

O
C CH2 NH2
(iv) N H (v) (vi) N
C
O

11. Amongs the following, the total number of compounds soluble in aqueous NaOH is :

H3C CH3
N COOH OCH2CH3 OH
CH2OH
(a) (b) (c) (d)

NO2 CH2CH3 COOH CH3


CH2OH
(e) (f) (g) (h)

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NH2 CH3

(i) (j) OH (k) SO3H () CH2–NMe2

CH3
CH3

NO 2

(m) HCCH (n) MeCOOH (o) HO NO2 (p) O N OH


2

NO 2

12. The number of groups showing +I effect = X

The number of groups showing –I effect = Y.

Find value XY e.g. if X = 3, Y = 4. Answer is 034

groups are given as follows :



(a) —Cl (b) —NH (c) —C–OH
O

(d) —N (e) (e) —CH (f) —C–O

O
+
(g) —CCl3 (h) —PH3 (i) —OH

Subjective Type Questions

13. Corelate P, Q, R, S with corresponding A, B, C.

H2
Pt
(P)
Heat of hydrogenation

A
H2 C
Pt B
(Q)
H2
Pt
(R)

H2
Pt
(S)

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14. Give increasing order of C-H bond energy of various C-H bonds in following compounds, mentioned by a to g

H g H
a CH3
H–H2C
f H
b H
H d e
H–H2C H
H
c

15. In the given pair of compounds select the one in each pair having lesser resonance energy :

(a) and (b) and


CH2
O OH

(c) and (d) and


NO2
N O
NO2
H

16. In which of the following pairs, indicated bond having less bond dissociation energy :

(a) and CH2 CH2 (b) CH3 C CH and HC CH

O
O
(c) CH2 CH CH CH2 and CH2 (d) and C
CH CH CH2 C
C CH3 NH2
C H2N NH2
CH2 CH2

O O O O

(e) C and C (f) C and C


Cl Cl CH3 Cl H2N NH2 H NH2

17. Compare the C–N bond-length in the following species :

NH2 H2N H2N

(A) (B) (C)

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18. Match each alkene with the appropriate heat of combustion :


Heats of combustion (kJ/mol) : 5293 ; 4658 ; 4650 ; 4638 ; 4632
(a) 1-Heptene (b) 2,4-Dimethyl -1-pentene (c) 2,4-Dimethyl-2-pentene
(d) 4,4-Dimethyl-2-pentene (e) 2,4,4-Trimethyl-2-pentene
19. Write decreasing order of heat of hydrogenation

(a) (b) (c)

(d)

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

(d) (e)

CH3 CH3
(iii) (a) (b)
CH3 CH3

O O
(iv) (a) (b)

CH3 H CH3 CH3


(v) (a) C C (b) C C
H CH3 H H

CH3 CH3
(vi) (b) CH2 CH CH (b) CH2 C
CH3 CH2 CH3

Statement Type Questions

20. Statement - I : C OEt C O C bond length a < b


a b
O O O
Because
Statement -II : More is the double bond character less is the bond length
(A) Statement-I is true, Statement-II is true and Statement - II is correct explanation for Statement - I.
(B) Statement-I is true, Statement-II is true and Statement - II is NOT the correct explanation for Statement - I.
(C) Statement-I is true, Statement-II is false.
(D) Statement-I is false, Statement-II is true.

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21. Statement - 1 : For the given two compounds - I is more acidic than compound - II.
NO2 CN
H3C CH3 H3C CH3

OH OH
(I) (II)
and
Statement - 2 : Due to presence of –CH3 group at ortho positions to –NO2 ; the plane of –NO2 deviates, w.r.t. plane of
ring.
(A) Statement - 1 is True, Statement - 2 is True ; Statement -2 is correct explanation for Statement -1.
(B) Statement - 1 is True, Statement - 2 is True ; Statement -2 is NOT a correct explanation for Statement -1.
(C) Statement - 1 is True, Statement - 2 is False.
(D) Statement - 1 is False, Statement - 2 is True.

22. Statement - 1 is more basic than


O N O O
N
(I) H
(II)

and
Statement - 2 : Lone pair electrons on nitrogen in compound (I) does not participate in resonance.
(A) Statement - 1 is True, Statement - 2 is True ; Statement -2 is correct explanation for Statement -1.
(B) Statement - 1 is True, Statement - 2 is True ; Statement -2 is NOT a correct explanation for Statement -1.
(C) Statement - 1 is True, Statement - 2 is False.
(D) Statement - 1 is False, Statement - 2 is True.

Comprehension Type Questions

Paragraph -1

CH3
(g)
(d) H
H–HN

H–CH2 (c)
(a) (e)
H H (b)
C C–H
OH
(f)

23 What will be the correct order of C–H bond energy :

(A) a > b > c d > e (B) b > e > c > a > d (C) e > b > a > c > d (D) d > c > a > b > e

24. What will be the correct order of acidic strength :

(A) e > f > g > b (B) f > e > g > b (C) b > g > e > f (D) b > g > f > e

25. What is the D.B.E. (Double bond equivalent) for the given compound :

(A) 4 (B) 6 (C) 8 (D) 10

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Paragraph -2

Aqueous Layer
Aqueous (Salt - B)
OH Organic Layer NaOH

COOH Aqueous
Organic Layer
NaHCO3
(Compound - C)
Aqueous Layer
(Salt - A)
Mixture of
3-compounds
in hexane

26. Identify salt ‘A’ ?

O Na+ COO Na+


+
Na
(A) (B) (C) (D) All of these

27. Identify compound ‘C’ ?

OH COOH OH

(A) (B) (C) (D)

COOH

Match the Column

28. Column-I Column-II

(Order) (Properties)

(A) > > (P) Heat of hydrogenation order

(B) > (Q) Heat of combustion order

(C) CH2=CH2 > CH3–CH=CH2 (R) Stability order

H H CHO
(D) > (S) Bond rotational energy barrier across (C=C)
H H
(T) Bond length of (C=C) bond

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29. Match the column :

Column-I Column-II

(Compounds) (Property)

(A) (P) Aromatic


N

(B) (Q) Nonaromatic

(C) (R) Heterocyclic


+
N
H H

(D) (S) Even number of -bond

(T) Odd number of -bond

30. Match the column :

Column-I Column-II

(A) < < (P) Correct order of stability of alkene

(B) < < (Q) Correct order of heat of combustion

(C) < < (R) Correct order of heat of hydrogenation

(D) < < (S) Correct order of C=C bond length

(T) Correct order of C=C bond energy

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31. Match the column :

Column-I Column-II

N
(A) (P) Aromatic
N
H

(B) (Q) Conjugate base is aromatic

(C) (R) Most acidic hydrogen in column-I


N

(D) (S) Most basic compound in column-I

(T) Non-aromatic

32. Match the column :

Column-I Column-II

COOH
CH3
(A) (P) React with Na

OH
O2N NO2
(B) (Q) React with NaOH

NO2

OH

(C) (R) React with NaHCO3

HO O

(D) (S) React with NaNH2

HO O

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33. Column-I Column-II

(A) and (P) (I) compound has more heat of

hydrogenation that (II)

(B) and (Q) (I) compound has more resonance energy that

(II) compound

(C) and (R) (I) compound is more stable than (II)

(D) and (S) (II) compound has more heat of hydrgenation

than (I)

(T) (II) compound has more degree of unsaturation

than (I)

34. Column-I Column-II

(A) (P) Aromatic

(B) (Q) Antiaromatic

(C) (R) Readily reacts with metal to form stable dianion

(D) C8H8 (S) Paramagnetic in nature due to presence of

unpiared electrons in molecular orbitals

(T) Diamagnetic in nature due to presence of even

electrons in molecular orbitals

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35. Match the Column


Column - I Column -II

OH

( A) (P) React with NaOH

OH

(B) (Q) React with NaHCO3

OH

(C) (R) React with NaH


NO2

OH
NO2

(D) (S) React with Na


NO2

(T) React with NaNH2


36. Match Column-I with Column - II.
Column - I (Compound) Column - II (pKa)

(A) HO F (P) 7.15

(B) HO Cl (Q) 10.14

(C) HO NO2 (R) 9.98

(D) HO CH3 (S) 9.38

(T) pKa is more than phenol

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