Organic Chemistry: Inductive and Resonance Effects
Organic Chemistry: Inductive and Resonance Effects
LEVEL-I
1. The inductive effect - 8. Which is the correct order of increasing basicity ?
(A) implies the atom’s ability to cause bond (A) CH3CH2 CH3 < CH3 CH2SH < CH3 CH2OH
polarization < CH3CH2NH2
(B) increases with increase of distance (B) CH3CH2 CH3 < CH3 CH2OH < CH3 CH2SH
(C) implies the transfer of lone pair of electrons < CH3CH2NH2
from more electronegative atom to the lesser (C) CH3CH2NH2 < CH3CH2SH < CH3 CH2 OH
electronegative atom in a molecule < CH3CH2CH3
(D) implies the transfer of lone pair of electrons (D) CH3CH2CH3 < CH3CH2OH < CH3CH2NH2 <
from lesser electronegative atom to the more CH3CH2SH
electronegative atom in a molecule
9. ‘M’ effect involves the delocalisation of –
2. In which of the following compounds hydroxylic
(A) electrons only
proton is the most acidic ?
(B) electrons only
F
(C) and both
(A) O (B) I O
H
H (D) (+)ve and (-) charge.
O O
H H 10. Which of the following contain + M & - effect -
(C) (D)
F F (A) O = CH – (B) – NO2
(C) – Cl (D) CH3 –
3. Decreasing – I power of given groups is -
(a) –CN (b) –NO2 (c) –NH2 (d) –F
11. The meta-directing power of the groups –NH2,
(A) b > a > d > c (B) b > c > d > a
(C) c > b > d > a (D) c > b > a > d –OCH3, –C6H5 and – NO2 follow the order
(A) –NH2 > –OCH3 > –C6H5 > –NO2
4. Express in decreasing order of (+) - (B) –NO2 > –C6H5 > –OCH3 > –NH2
(a) CH3CH2 – CH2 – (b) CH3 – (C) –OCH3 > –NH2 > –C6H5 > –NO2
CH3 (D) –OCH3 > –NO2 > –NH2> –C6H5
CH3
(c) CH3–C–CH2–CH3 (d) CH3–C– 12. Which of the following pairs of structures do
CH3 not represent resonating structures -
CH3–CH–CH2– O OH
(e) (A)
CH2CH3 CH3 – C – CH3 ; CH3 – C = CH2
Correct answer is -
(A) (c) > (d) > (e) > (a) > (b)
(B) (d) > (a) > (b) > (c) > (e) (B) O ; O
(C) (a) > (b) > (c) > (d) > (e)
(D) (a) > (b) > (c) > (e) > (d) OH OH
(C)
CH 3 – C – CH3 ; CH3 – C – CH 3
5. Which among the given acid has lowest pKa
value -
(A) Chloroacetic acid (B) Bromoacetic acid CH3 –C–OH ; CH3–C=OH
(C) Nitroacetic acid (D) Cyanoacetic acid (D)
O O
6. Arrange basicity of the given compounds in
decreasing order - 13. In which of the following structure the
(a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 electrophilic attack of nitronium ion will place
(c) CH C – NH2 at m-position
(A) a > b > c (B) a > c > b
(C) c > b > a (D) b > c > a O– CF3 Cl NO2
7. Consider following acid
ClCH2COOH, CH3COOH, CH3CH2COOH
I II III I II III IV
Correct order of their pH value is–
(A) III < II < I (B) I < II < III (A) only IV (B) II and IV
(C) I < III < II (D) II < I < III (C) II, III, IV (D) only I
Page # 86 GOC
14. Which of the following is the strongest base - 21. More will be the number of ‘H’ greater will be the -
(A) + M effect
(B) conjugative effect
(A) N (B) (C) Hyper conjugative effect
N (D) – I effect
H
27. Which statement is correct for electromeric 35. Which of the following statements is wrong ?
effect - (A) a tertiary free radical is more stable than a
(A) It is a temporary effect secondary free radical
(B) It is the property of bond (B) a secondary free radical is more stable than
(C) It takes place in presence of reagent, i.e., a primary free radical
electrophile or nucleophile
(C) atertiary carbonium ion is more stable than
(D ) All are correct
a secondary carbonium ion
(D) a primary carbonium ion is more stable than
28. Which of the following exhibit electromeric
effect - a secondary carbonium ion
(A) alkanes (B) aldehydes
(C) alkyl halides (D) alkyl amines 36. Consider the following carbanions -
29. Shifting of electron of a multiple bond under (a) CH – C H 2 (b) CH2 = C H (c) CH C
3
the influence of a reagent is called - Correct order of stability of these carbanions is -
(A) I–effect (B) M–effect (A) a > b > c (B) b > a > c
(C) E–effect (D) R–effect
(C) c > b > a (D) c > a > b
32. In CH 3 CH 2 OH, the bond that undergoes 38. Which of the following carbocation is most
heterolytic cleavage most readily is -
stable
(A) C—C (B) C—O
(C) C—H (D) O—H
(A) CH2 (B)
33. Which among the following statements are
correct ?
(C) (D) CH2
(1) Energy needed for homolytic bond fission
is less than that required for the heterolytic
bond fission 39. Carbon free radicals are -
(2) Homolytic bond fission gives neutral species
(A) Diamagnetic (B) Paramagnetic
which is paramagnetic in character
(C) Ferromagnetic (D) Non magnetic
(3) Energy needed for heterolytic bond fission
is less than that required for the homolytic
bond fission. 40. Correct order of stability is –
(4) Heterolytic bond fission takes place in non CH2 CH2 CH2 CH2
polar solvents
(A) Only 1 (B) 1 and 3
(C) 1 and 2 (D) 1, 2 and 4
OCH3 OH NH2 Cl
34. Which of the following statements is correct? I II III IV
(A) + group stabilised carbocation (A) I > II > III > IV
(B) + group destabilised carbocation (B) III > I > II > IV
(C) – group stabilised carbocation (C) IV > I > II > III
(D) – group destabilises carbanion (D) II > III > I > IV
Page # 88 GOC
41. The order of stability of the following carbanion is : 46. Which of the following statements are correct
for nucleophile :
(A) All negatively carged species are
R C H2 nucleophile
( I) IV (B) Nucleophiles are Lewis bases
(A) I > II > III > IV (B) I > III > II > IV (C) Alkenes, alkynes, benzene and pyrrole are
(C) IV > III > II > I (D) III > IV > I > II nucleophiles
(D) All are correct
42. Which free radical is the most stable :
47. Which among the following species is an
(A) C6H5— C H 2 ambident nucleophile ?
(A) CH3– C H 2 (B) CH2=CH2
(B) CH2=CH— C H 2 ..
(C) CN (D) N H 3
(C) CH3— C H —CH3
CH3–C–CH3 48. Which has maximum stability ?
(D) +
CH3 + CH2
CH2
43. Rank the following radicals in order of
decreasing stability
(a) (b)
NO2
I II III IV +
(A) III > II > I > IV (B) III > II < I < IV CH2
(C) II > III > II > IV (D) III < II < I < IV +
CH2
44. Reactivity of C—H bond (abstraction of H) NO2
CH2=CH—H, CH3—H, CH3CH2—H (c) (d)
(i) (ii) (III)
(CH3)2CH—H (CH3)3C—H,
NO2
(IV) (V)
(A) II < III < I < IV < V
(B) I > II > III > IV > V
49. Which of the following reaction intermediates
(C) I < II < III < IV < V
are electrophilic in character ?
(D) I < II < IV < III < V
(a) Carbocation (b) Carbanion
45. Rank the following free radicals in order of (c) Free radicals (d) Carbenes
decreasing stability : (A) Only b (B) a and c
(C) a, c and d (D) a, b, c and d
(I) C H C H C6H5
6 5
50. Which among the following compounds behave
(II) C6H5– C H –CH = CH2 both as an electrophile as well as a nucleophile:
(III) CH3– C H –CH3 (a) CH2=CH2 (b) CH2=CH– C H 2
(IV) C6H5 – C H – CH3 O O
(c) (d)
CH3–C–CH3 CH3–C–Cl
(V) CH3CH = CHCH2 C H (A) Only a (B) a and b
2
(C) c and d (D) b, c and d
(VI) CH3–CH2–C–CH3
CH3
51. Which of the following has the highest
(A) I > II > III > IV > V > VI nucleophilicity -
(B) VI > V > IV > III > II > I (A) F– (B) OH–
(C) I > II > IV > VI > III > V
(D) I > IV > VI > V > II > III (C) CH 3 (D) NH
2
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52. Arrange the following nucleophiles in the order 61. Carbocations may be stabilised by -
of their nucleophilic strength - (A) -bonds only at allylic position
(A) OH–> CH3COO– > –OCH3 > C6H5O– (B) bonds only at vinylic position
(B) CH3COO– < C6H5O– < –OCH3 < OH–
(C) bonds at allylic and nonallylic position also
(C) C6H5O– < CH3COO– < CH3O– < OH–
(D) CH3COO– < C6H5O– < OH–< CH3O– (D) – I effect
53. Correct order of leaving group tendency - 62. In the anion HCOO–, the two carbon-oxygen
(A) – > Br – > Cl– > F–
bonds are found to be equal length. What is
(B) F– > Cl– > Br – >
the reason for it -
(C) Cl– > F – > Br – > –
(A) the C=O bond is weaker than the C—O bond
(D) – > Cl– > Br – > F
67. Arrange in decreasing order of pKb - 73. Which one of the following orders is correct
(a) F–CH CH COOH regarding the –I effect of the substituents ?
2 2
Cl–CH–CH2–COOH (A) –NR2 < –OR > –F
(b) (B) –NR2 > –OR > – F
Cl
(C) –NR2 < –OR < –F
(c) F–CH2–COOH (D) –NR2 > –OR < –F
(d) Br–CH2–CH2–COOH
Correct answer is -
74. Increasing order of acid strength among
(A) (b) > (d) > (a) > (c)
p-methoxyphenol, p-methylphenol, and
(B) (a) > (c) > (d) > (b)
p-nitrophenol is -
(C) (c) > (b) > (a) > (d)
(A) p-nitrophenol, p-methoxyphenol,
(D) (d) > (b) > (a) > (c)
p-methylphenol
(B) p-methylphenol, p-methoxyphenol,
68. The strongest base is -
p-nitrophenol
CH3–N–CH3 H2N NH (C) p-nitrophenol, p-methylphenol,
C
(A) (B) p-methoxyphenol
CH3 NH2 (D) p-methoxyphenol, p-methylphenol,
C6H5–N–C6H5 p-nitrophenol
(C) (D) CH3—NH—CH3
C6H5
75. Consider the following carbanions :
69. In which of the following cases, the carbocation
..
(I) is less stable than the carbocation (II) ? (I) H3CO CH2
(A) C H C H (I), CH CH C H ( II)
..
6 5 2 2 2
(II) O2N CH2
+ +
CH2 CH2
(B)
..
(I), (II)
(III) CH2
(C) CH 2 C H(I), CH 3 C H 2 (II)
..
(IV) H3C CH2
(D) H 3C C H 2 (I), CH 2 C H 2 (II) Correct order of stability is -
| (A) II > III > IV > I (B) III > IV > I > II
F (C) IV > I > II > III (D) I > II > III > IV
77.
(c) C H 3 (d) N H 2 (II) (III)
(I)
Arrange these nucleophilic species in their Arrange following acid in decreasing order of
decreasing order of nucleophilicity - [H+] conc.
(A) c > d > b > a (B) b > a > c > d (A) I > II > III (B) II > III > I
(C) a > b > c > d (D) c > a > b > d (C) II > I > III (D) III > II > I
GOC Page # 91
78. Arrange Increasing order of their Ka value. 85. Stability of following radical is
oxalic acid, succinic acid, CH3 CH2•
I II
•
malonic acid, adipic acid CH2= C H , C H 2 –CH=CH2
III IV
(all dibasic) I II III IV
(A) III < II < I < IV (B) II < III > I > IV (A) II > III > II > IV (B) III > II > I > IV
(C) I > III > II > IV (D) II > I > III < IV (C) III < II < I < IV (D) I < IV < II < III
79. Most powerful leaving group is- 86. Increasing order of the following for SE
(A) NH2– (B) OH– CH3 NO2 OH
(C) CH3– (D) F–
92. Which of the following shows the correct order 98. The order of decreasing stability of the cations
of decreasing basicity in aqueous medium
(A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3 CH 3 C HCH 3 CH 3 C HOCH 3 CH 3 C HCOCH 3
(B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3 I II III
is -
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3
(A) III > II > I (B) I > II > III
(D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N
(C) II > I > III (D) I > III > II
93. The correct order of increasing basicity is - COOH
(A) pyrrole < pyridine < Me3N < Et3N
(B) pyridine < pyrrole < Et3N < Me3N
(C) pyrrole < Et3N < Me3N < pyridine 99. , pKa value of the compound decreases
(D) Me3N < Et3N < pyridine < pyrrole X
if X is:
94. Give the correct order of decreasing basicity (A) –NO2 (B) – NH2
of the following compounds, (C) – OH (D) – OCH3
C6H5NH2 (C6H5)2NH (C6H5)3N C6H11NH2
I II III IV 100. Which type of hybrid orbitals do C and N use in
the formation of C–N bond in pyrrole?
(A) I > II > III > IV (B) IV > III > II > I
(C) IV > I > II > III (D) III > II > I > IV :NH
(A) sp2 and sp2 (B) sp2 and sp3
95. The correct order of stability of the following
(C) sp and sp3 (D) sp and sp2
carbocations is -
101. Weakest base among the following is:
(A) CH 3CH 2 C H 2 > CH 2 CH – C H 2 >
CH2= CH C HCH 3 > CH2=CH C (CH3)2
(A) NH (B) NH NH
(B) CH2= CH C H 2 > CH 3CH 2 C H 2 > (C) NH2 (D) N
CH 2 CH C(CH 3 ) 2 > CH2 = CH C HCH 3
102. Which nitrogen in LSD is most basic
(C) CH 2 CH C(CH 3 ) 2 > CH2 = CH C HCH 3 >
O
(1) (3)
CH 2 CH C H 2 > CH 3CH 2 C H 2 C–N(C2H5)2
H–N (2)
(D) CH2= CH C HCH 3 > CH 2 CH C(CH 3 ) 2 N
> CH3CH2– C H 2 > CH2 = CH C H 2 CH3
(A) 1 (B) 2
(C) 3 (D) All are equally basic
96. The order of reactivity of the following alcohols
towards concentrated HCl is - 103. Different hydrogens in
OH
a b b c d e f
F CH 3 CH = CH—CH 2 —CH 2 —CH(CH 3 ) 2 are
OH , F represented by alphabets. Arrange them in
I II decreasing order of reactivity towards radical
OH OH substitution :
Ph
(A) c > a > e > d > f > b
, (B) f > b > a > c > d > e
III IV (C) b > c > a > f > d > e
(A) I > II > III > IV (B) I > III > II > IV (D) a > b > c > d > e > f
(C) IV > III > II > I (D) IV > III > I > II 104. Which of the following most readily reacts with
AgNO3 to give ppt.:
97. Increasing order of acidity in para methyl (I),
chloro (II), amino (III), and nitro (IV) benzoic (A) Br (B) CH=CH–CH2Br
acids is - Br
(A) III < II < I < IV (B) I < II < IV < III (C) (D) Br
(C) III < I < II < IV (D) II < I < III < IV
GOC Page # 93
105. Arrange the following in Decreasing of their 108. Benzoic acid is less acidic than salicylic acid
basic nature. because of -
NH2 (A) Hydrogen bond (B) Inductive effect
(C) Resonance (D) none of these
106. Which one of the carbanions is most stable? (A) b>a>c (B) a>b>c
(C) c>b>a (D) None
CH2
CH2
110. Compare the stability of the following
(A) NO2 (B) carbocation
+
NO2 CH2 +
CH2 +
CH2
CH2
CH2 (a) (b) (c)
(C) CN (D) Cl
F
CN (A) c>a>b (B) a>c>b
(C) a>b>c (D) None
7. The stabilization due to resonance is maximum in 14. Consider the following carbocations
(a) CH3O CH2 (b) CH2
(A) (B) (C) (D)
H (c) CH3 CH2 (d) CH3— C H 2
8. CH 3 CH 2 CH 2 CH 2 — C ; CH3 C CH3 ;
H The relative stabilities of these carbocations
H are such that :-
(A) d < b < c < a (B) b < d < c < a
H
CH3CH2CH2 — C ; CH3 (C) d < b < a < c (D) b < d < a < c
CH3
Among these carbocations : 15. Hydrogen attached to sp3 carbon in cyclopentadiene
(A) One is secondary carbocation can be easily removed as what :-
(B) One is tertiary carbocation (A) Hydride ion (B) Hydrogen molecule
(C) Two are primary carbocations (C) Proton (D) Hydrogen atom
(D) Two are tertiary carbocations 16. Tautomerism is due to :-
9. Most stable carbanion is :- (A) Delocalization of sigma electrons
(B) Delocalization of pi electrons
(A) HC C (B) H2C CH (C) Migration active–H–atom
CH3 (D) None is correct
(C) CH3–C CH2 (D) CH3–C CH 17. Among the following, the strongest base is :-
CH3 CH3 (A) C6H5NH2 (B) p–NO2–C6H4NH2
(C) m–NO2–C6H4NH2 (D) C6H5CH2NH2
10. (a) CH2 CH—CH CH2
18. Correct acidic nature is :-
(b) CH3—CH CH2
(A) CH3OH < CH3SH < CH3NH2
(c) CH3—CH3
C—C single bond distance would be :- (B) CH3NH2 < CH3OH < CH3SH
(A) a (146 pm) b (151 pm) c (153 pm) (C) CH3SH < CH3OH < CH3NH2
(B) a (151 pm) b (146 pm) c (153 pm) (D) None of these
(C) a (146 pm) b (153 pm) c (151 pm) 19. Which of the following carbonyl compound is
(D) a (153 pm) b (146 pm) c (151 pm) least reactive towarts N.A.R. :-
11. In HC C (acetylide ion) and CH2 CH (vinyl (A) C6H5CHO (B) CH3CHO
anion) :- (C) C6H5COCH3 (D) C6H5COC6H5
(A) HC C is less basic 20. Which of the following order is correct for the
(B) HC C– is more basic decreasing reactivity towards E.S.R. the
(C) Basic strength is the same following compounds :-
(D) None
CH3 COOH NO2
12. In which of the following compounds carbon–
chlorine bond distance is minimum :-
(A) CH3—Cl (B) C6H5—CH2—Cl I II III IV
(C) CH2 CH—Cl (D) CH2 CH—CH2—Cl (A) I > II > III > IV (B) II > III > IV > I
(C) I > III > II > IV (D) III > I > II > IV
13. Consider the following statements :-
21. The correct order of decreasing basic strength is
(a) CH O C H is more stable than CH 3 C H 2 NH2
3 2
(b) Me 2 C H is more stable than CH CH C H
3 2 2
N N N
I II III IV
(c) CH2 CH— C H 2 is more stable than CH 3 CH 2 C H 2
(A) I > II > III > IV (B) II > III > I > IV
(C) II > IV > I > III (D) II > III > IV > I
(d) CH2 C H is more stable than CH 3 C H 2
22. Which of the following is most acidic :-
of these statements :-
(A) phenol (B) benzyl alcohol
(A) a and b are correct(B) c and d are correct
(C) m-chloro phenol (D) cyclohexanol
(C) a, b and c are correct(D) b, c and d are correct
GOC Page # 95
23. The correct order of increasing dissociation 29. The strongest deactivating effect on aromatic
constant [Ka] of the following compound is :- ring is
(A) –CH2Cl (B) –OCH3
OH OH (C) –CH3 (D) –CCl3
OH OH
NO2 NO2 30. Which of the following is maximum reactive
NO2
towards E.S.R. :-
38. Arrange the following in correct order of acidic 45. Which of the following pairs are not resonating
strength : structures –
(I) CH3—NO2 (II) NO2—CH2—NO2 (A) ;
(III) CH3—CH2—NO2 (IV) NO2 CH NO2 (B) CH3–CH=CH–CH3 ; CH3–CH2–CH=CH2
NO2 (C) ;
(A) IV > II > I > III (B) IV > II > III > I
(C) III > I > II > IV (D) III > I > IV > II (D) All the above
39. The correct order of stability of given 46. Which is incorrect stability order :-
carbanions will be :-
(A) CH2 = CH – CH 2 > CH3 – CH – CH3
CH3–CH2 CH 2=CH HC C
(III) (B) CH2 = CH < CH3 – CH 2
(I) (II)
(A) I > II > III (B) III > II > I (C) >
(C) I > III > II (D) II > I > III
40. Which of the following is most stable (D) CH3 – CH 2 > CH3O – CH 2
carbocation:- 47. Which compound shows dipole moment :-
(A) 1,4–Dichloro benzene
(A) (B) (B) trans–2–Butene
(C) trans–1–Chloro propene
(D) trans–1,2–Dichloro ethene
48. Mesomeric effect is due to :-
(C) CH2 (D) CH2=CH–CH2 (A) Delocalization of es–
(B) Delocalization of es–
41. Select the correct option for stability of (C) Migration of H – atom
following resonance structures :- (D) Migration of proton
49. Which is most basic among the following :-
(A) CH3NH2 (B) CH3CH2NH2
O CH2 , O CH2 , O CH2 (C) NH3 (D) (CH3)2CHNH2
x y z 50. Which is Aromatic compound :-
(A) x > y > z (B) z > y > x
(C) y > x > z (D) y > z > x
42. The dipole moment of vinyl chloride is lower (A) (B)
than that of methyl chloride. This is due to :-
(A) Resonance effect (B) Inductive effect
(C) Electromeric effect (D) Hyperconjugation N
43. Which of the following is the strongest base :- (C) (D) 2 and 3 both
NH
(A) (B) 51. Which of the following is the most acidic
compound :-
(A) CH2 = CH2 (B) HC CH
(C) (D) (C) (D)
44. The oxygen atom in phenol – 52. Which of the following compounds will give
maximum enol content –
(A) exhibits only inductive effect
(B) exhibits only resonance effect O O
(C)has more dominating resonance effect than (A) H–C–CH2–C–CH3 (B)
inductive effect
(D) has more dominating inductive effect than
(C) (D)
resonance effect
GOC Page # 97
53. Which of the following is least stable :– 58. Which of the following is least basic :–
NH2
(A) (B)
(A) (B) (C) (D)
(C) (D) Cl
59. Among the following the pKa is minimum for :–
54. Identify correct order of reactivity for
(A) C6H5OH (B) HCOOH
electrophilic substitution reaction of the
following compounds :– (C) C2H5OH (D) CH3CCH
60. Among the following the aromatic compound is –
(A) < < <
(A) (B)
(C) (D)
(A) C1–H (B) C2–H
(C) C3–H (D) C4–H
56. Which of the following is most stable alkene :-
O
(A) (B) 63. O–C NO2
Product is :-
O NO2
(C) (D) (A) O–C
O
57. Which one of the following resonating
structures of 1–methoxy–1,3–butadiene is least (B) O–C NO2
stable :–
O
(A) H2–CH=CH–CH= –CH3 (C) O2N O–C
(B) CH2=CH– H–CH= –CH3 NO2
O
(C) H2– H–CH=CH–O–CH3 (D)
(D) CH2=CH–CH=CH–O–CH3 O–C
Page # 98 GOC
64. Which of the following acid – base reaction is 67. Select the correct option for stability of
not suitable following carbanions :
CH3
H
– –
N NH N N CH3 ; CH CH ; CH–C
(A) H
H 6 5 2 3
–
–
–
–
H
–
–
H O O
O O
N (B) CH3–CH=CH–CH3 and CH2=CH–CH2–CH3
N
(C) H
N (C) H–CNH and H– C =NH
N
H (D) and
NH2 NH2
H
(D) H2N–C H2N–C
NH NH2 69. Which of the following contains three pair of
electrons :
(A) Carbanion (B) Carbocation
(C) Carbon free radical(D) None
HOOC OH
NaNH2
70. Which is an aromatic compound :-
65. 1mole product is
HC C CH2OH N–N
(A) (B) H 3C CH3
O
HOOC ONa
N–CH 3
(C) (D)
(A) H 3C–N
HC C CH2OH O
71. The correct order of stability of following carbon
free radical is :-
HOOC OH
(CH3 )3 C CH2 CH 3CH 2 CH 2 CH 3
(B) (1) (3) (4)
HC C CH2ONa (2)
(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1
(C) 2 > 3 > 1 > 4 (D) 2 > 1 > 3 > 4
HOOC OH 72. Which of the following is not a pair of resonating
structures :-
(C)
NaC C CH2OH (A) O and O
1. In the following benzyl/alkyl system 7. Amongst the following the most basic
compound is - [AIEEE-2005]
R – CH = CH2 or R (A) aniline (B) benzylamine
(C) p–nitroaniline (D) acetanilide
(R is alkyl group) [AIEEE-2002] 8. The increasing order of stability of the following
increasing order of inductive effect is - free radicals is - [AIEEE 2006]
(A) (CH3)3 C – > (CH3)2 CH – > CH3CH2—
(B) CH3CH2 – > (CH3)2 CH – > (CH3)3C — (A) (C6H5)3 C < (C6H5)2 C H < (CH3)3 C < (CH3)2 C H
(C) (CH3)2 CH – > CH3CH2 – > (CH3)3C—
(D) (CH3)3C – > CH3CH2 – > (CH3)2CH— (B) (C6H5)2 C H < (C6H5)3 C < (CH3)3 C < (CH3)2 C H
2. The correct order of increasing basic nature of (C) (CH3)2 C H < (CH3)3 C < (C6H5)3 C < (C6H5)2 C H
the bases NH3, CH3NH2 and (CH3)2NH is -
(A) NH3 < CH3NH2 < (CH3)2NH [AIEEE-2003] (D) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3 C
(B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH 9. CH3Br + Nu– CH3 – Nu + Br–[AIEEE 2006]
(D) (CH3)2NH < NH3 < CH3NH2 The decreasing order of the rate of the above
reaction with nucleophiles (Nu–) A to D is
3. Rate of the reaction [AIEEE-2004-2005] [Nu– = (A) PhO–, (B) AcO–, (C) HO–, (D) CH3O]
(A) D > C > B > A (B) A > B > C > D
O O
R–C + Nu R–C + Z (C) B > D > C > A (D) D > C > A > B
Z Nu 10. The correct order of increasing acid strength
is fastest when Z is - of the compounds [AIEEE 2006]
(A) Cl (B) NH2 (a) CH3CO2H (b) MeOCH2CO2H
(C) OC2H5 (D) OCOCH3
Me
(c) CF3CO2H (d) CO2H is
4. Consider the acidity of the carboxylic acids : Me
(a) PhCOOH [AIEEE-2004]
(A) d < a < c < b (B) d < a < b < c
(b) o – NO2C6H4COOH (C) a < d < c < b (D) b < d < a < c
(c) p – NO2C6H4COOH
(d) m – NO2C6H4COOH 11. Which one of the following is the strongest
Which of the following order is correct ? base in aqueous solution ? [AIEEE-2007]
(A) Trimethylamine (B) Aniline
(A) a > b > c > d (B) b > d > c > a
(C) b > d > a > c (D) b > c > d > a (C) Dimethylamine (D) Methylamine
5. Which of the following is the strongest base - 12. Presence of a nitro group in a benzene ring :
[AIEEE-2004] (A) activates the ring towards electrophilic
substitution [AIEEE 2007]
(A) NH2 (B) NHCH3 (B) renders the ring basic
(C) deactivates the ring towards nucleophilic
substitution
NH2
(C) (D) CH2NH2 (D) deactivates the ring towards electrophilic
CH3 substitution
6. The decreasing order of nucleophilicity among 13. Arrange the carbanions, (CH 3 ) 3 C , C Cl 3 ,
the nucleophiles [AIEEE-2005]
(CH 3 ) 2 C H , C 6 H 5 C H 2 , in order of their
CH3C–O– –
(a) (b) CH3O decreasing stability - [AIEEE 2009]
O
(A) (CH3)2 C H > C Cl 3 > C6H5 C H 2 > (CH3)3 C
O
–
– S–O (B) C Cl 3 > C6H5 C H 2 > (CH3)2 C H > (CH3)3 C
(c) CN (d) H3C is -
O (C) (CH3)3 C > (CH3)2 C H >C6H5 C H 2 > C Cl 3
(A) (d), (c) , (b) , (a) (B) (a), (b), (c) , (d)
(C) (c) , (b) , (a) , (d) (D) (b), (c) , (a) , (d) (D) C6H5 C H 2 > C Cl 3 > (CH3)3 C > (CH3)2 C H
Page # 100 GOC
14. Consider thiol anion (RS) and alkoxy anion 21. Which of the following carbonium ion is most
(RO). Which of the following statement is stable [RPMT-2001]
correct ? [AIEEE 2011] (A) Ph3C+ (B) (CH3)3 C+
(C) (CH3)2 CH+ (D) CH2 CH—CH2+
(A)RS is less basic but more nucleophilic than RO
(B) RS is more basic and more nucleophilic 22. In benzene C—C bond length between all
than RO carbons are equal because of :- [RPMT-2001]
(A) Tautomerism (B) sp2 hybrization
(C) RS is more basic but less nucleophilic than RO
(C) Isomerism (D) Resonance
(D) RS is less basic and less nucleophilic than RO
23. Which compound shows dipole moment :-
15. The correct order of acid strength of the (A) 1,4–dichloro benzene [RPMT-2002]
following compounds is : [AIEEE 2011] (B) cis 1,2–dichloro ethene
A. Phenol B. p-Cresol (C) trans1,2 di–chloro ethene
C. m-Nitrophenol D. p-Nitrophenol (D) trans–2–butene
(A) D > C > A >B (B) B > D > A > C 24. Aryl halide less reactive than alkyl halide
(C) A > B > D >C (D) C > B > A > D towards nucleophilic substitution because :-
(A) Less stable carbonium ion [RPMT-2002]
16. The non aromatic compound among the (B) Due to large C–Cl bond energy
following is - [AIEEE 2011] (C) Inductive effect
(D) Resonance stabilisation and sp 2
hybridisation of C attached to halide
(A) (B)
S 25. Correct order of acidic strength is
[RPMT-2003]
(A) HCOOH > CH3COOH > C2H5COOH
(C) (D) (B) C2H5COOH > CH3COOH > HCOOH
(C) HCOOH > C2H5COOH > CH3COOH
(D) CH3COOH > HCOOH > C2H5COOH
17. The number of e– in benzene are :-
26. Which of the following has maximum pKa :-
(A) 8e– (B) 3e– [RPMT-2000] (A) CH2FCOOH [RPMT-2006]
(C) 6e – (D) 2e– (B) CH2ClCOOH
18. The polarity order in CH3I, CH3Br and CH3Cl (C) CH3COOH
(D) HCOOH
molecules will be:- [RPMT-2000]
(A) CH3Br > CH3Cl > CH3I 27. Polarization in acrolein as :- [AIPMT-2000]
(B) CH3I > CH3Br > CH3Cl
(C) CH3Cl > CH3Br > CH3I (A) CH2 CH CHO (B) CH2 CH CHO
(D) CH3Cl > CH3I > CH3Br
(C) CH2 CH CHO (D) CH2 CH CHO
19. Which of the following structure is wrong :-
28. Correct order of stability is :- [AIPMT-2000]
[RPMT-2001]
(A) 1–butene > trans–2–butene > cis–2–butene
(B) trans–2–butene > 1–butene > cis–2–butene
(A) CH3 CH O H (B) CH3 CH2 NH
(C) trans–2–butene > cis–2–butene > 1–butene
CH2 CH2 (D) cis–2 butene > trans–2–butene > 1–butene
(C) C (D) CH3—O N O
H O
..
29. CH2 C CH3 and CH2 C CH3 are :-
31. Which of the follwing orders of acid strength is 39. Which amongst the following is the most stable
correct :- [AIPMT-2003] carbocation :- [AIPMT-2005]
(A) RCOOH > ROH > HOH > HC CH
(A) CH CH (B) CH
(B) RCOOH > HOH > ROH > HC CH 3 2 3
36. The strongest base among the following is :- 42. Which of the following is more basic than aniline
(A) Diphenyl amine [AIPMT-2006]
(A) (B) [AIIMS-2004] (B) Triphenyl amine
(C) p-nitro aniline
N N
(D) Benzyl amine
H
43. Which of the following presents the correct
order of the acidity in the given compounds :
NH2
N [AIPMT-2007]
(C) (D) (A) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH
H
(B) BrCH2COOH > ClCH2COOH > FCH2COOH >CH3COOH
37. Among the following the dissociation constant (C) FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
is highest for [AIIMS-2004] (D) CH3COOH > BrCH2COOH > ClCH2COOH> FCH2COOH
(A) C6H5OH (B) C6H5CH2OH 44. For the following : [AIPMT-2007]
(C) CH3C CH (D) CH3 NH 3 Cl– (a) I– (b) Cl– (c) Br–
the inceasing order of nuclcophilicity would be :
38. Among the following the aromatic compound is
(A) Cl– < Br– < I– (B) I– < Cl– < Br–
[AIIMS-2004]
(C) Br– < Cl– < I– (D) I– < Br– < Cl–
(A) (B)
45. The order of decreasing rectivity towards
electrophilic reagent for the following :
[AIPMT-2007]
(a) Benzene (b) Toluene
(C) (D) (c) Chloro benzene (d) Phenol
(A) b > d > a > c (B) d > c > b > a
(C) d > b > a > c (D) a > b > c > d
Page # 102 GOC
Cl
OH (A) [AIPMT-2015]
(A) (B)
(B)
CH2OH NO2
(C) (D)
(C)
47. The stability of carbanions in the following:-
..
(a) RC
C (b)
(D)
(c) R2C=CH (d) R3C–CH2 49. Which of the following statements is not correct
is in the order of:- [AIPMT-2008] for a nucleophile ? [AIPMT-2015]
(A) (d) > (b) > (c) >(a) (A) Nucleophile is a Lewis acid
(B) (a) >(c) >(b) >(d) (B)Ammonia is a nucleophile
(C) (a) > (b) > (c) > (d) (C) Nucleophiles attack low e. density sites
(D) (b) > (c) > (d) >(a) (D) Nucleophiles are not electron seeking.
GOC Page # 103
ANSWER KEY
LEVEL-I
1. A 2. D 3. A 4. A 5. C 6. A 7. B
8. A 9. A 10. C 11. B 12. A 13. B 14. A
15. C 16. B 17. D 18. D 19. B 20. B 21. C
22. C 23. D 24. A 25. B 26. C 27. D 28. B
29. C 30. C 31. D 32. D 33. C 34. A 35. D
36. C 37. D 38. B 39. B 40. B 41. D 42. A
43. A 44. C 45. C 46. D 47. C 48. A 49. C
50. C 51. C 52. D 53. A 54. A 55. C 56. D
57. D 58. D 59. D 60. B 61. A 62. B 63. B
64. A 65. A 66. A 67. C 68. B 69. C 70. A
71. C 72. A 73. C 74. D 75. A 76. C 77. A
78. C 79. D 80. A 81. D 82. B 83. D 84. C
85. D 86. C 87. A 88. A 89. C 90. B 91. D
92. C 93. A 94. C 95. C 96. C 97. C 98. C
99. A 100. A 101. D 102. B 103. A 104. D 105. B
106. A 107. B 108. D 109. A 110. B
LEVEL-II
1. C 2. C 3. D 4. A 5. A 6. C 7. D
8. B 9. A 10. A 11. A 12. C 13. C 14. A
15. C 16. C 17. D 18. B 19. D 20. C 21. D
22. C 23. D 24. D 25. B 26. A 27. C 28. B
29. D 30. B 31. A 32. A 33. C 34. C 35. D
36. D 37. B 38. A 39. B 40. A 41. C 42. A
43. D 44. C 45. B 46. D 47. C 48. B 49. D
50. D 51. D 52. B 53. B 54. D 55. B 56. B
57. C 58. A 59. B 60. C 61. B 62. B 63. C
64. A 65. D 66. D 67. B 68. B 69. B 70. B
71. D 72. D 73. C
LEVEL-III
1. A 2. A 3. A 4. D 5. D 6. D 7. B
8. D 9. D 10. B 11. C 12. D 13. B 14. A
15. A 16. D 17. C 18. C 19. D 20. D 21. A
22. D 23. B 24. D 25. A 26. C 27. D 28. C
29. A 30. D 31. B 32. D 33. D 34. C 35. A
36. C 37. D 38. A 39. C 40. A 41. B 42. D
43. C 44. A 45. C 46. A 47. C 48. A 49. A