TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY

RISHI MEDICAL & IIT ACADEMY

Near New Rishi School, Bayammathota, Mahabubnagar KASSA

09. RX + I − → R − I + X − . This is an
01. example of
1) Nucleophilic addition
2) Nucleophilic substitution
3) Electrophilic addition
4) Elimination reaction
10. Which of the following reactions is an
example of nucleophilic substitution
The above reaction proceeds through reaction
1) Nucleophilic substitution 1) RX + KOH → ROH + KX
2) Electrophilic substitution 2) 2 RX + 2 Na → R − R + 2 NaX
3) Free radical substitution 3) RX + H 2 → RH + HX
4) More than one of the above processes 4) RX + Mg → RMgX
02. The reaction is
11. The most common type of reaction in
CH 2 = CH − CH 3 + HBr → CH 3 − CHBr − CH 3
aromatic compounds is
1) Nucleophilic addition 1) Elimination reaction
2) Electrophilic substitution 2) Addition reaction
3) Electrophilic addition 3) Electrophilic substitution reaction
4) Free radical addition 4) Rearrangement reaction
03. Which of the following is an example of 12. Nucleophilicity order is correctly
elimination reaction? represented by
1) Chlorination of methane − − − −
2) Dehydration of ethanol 1) CH 3 < NH 2 < HO < F
3) Nitration of benzene − − − −
2) CH 3 = NH 2 > HO = F
4) Hydroxylation of ethylene − − − −
04. Conversion of CH4 to CH3Cl is an example 3) CH 3 > NH 2 > HO > F
of which of the following reaction. − −
4) NH 2 > F > HO > CH 3
− −

1) Electrophilic substitution
13. The correct increasing order of reactivity
2) Free radical addition
for following molecule towards E.S.R
3) Nucleophilic substitution
4) Free radical substitution
05. Following reaction,
( CH 3 )3 CBr + H 2O → ( CH 3 )3 COH + HBr is
an example of
1) Elimination reaction
2) Free radical substitution
3) Nuclophilic substitution
4) Electrophilic substitution
06. Bromination of alkans involve
1) Carbanions 2) Carbocations
3) Carbenes 4) Free radicals
07. Which of the following cannot undergo
nucleophilic substitution under ordinary
conditions
1) Chlorobenzene 2) Ter.butyl chloride
3) Isopropyl chloride 4) None of these
08. Which one will give nucleophilic addition 1) 3 > 4 > 2 > 1 2) 4 > 3 > 2 > 1
reaction 3) 1 > 2 > 3 > 4 4) 1 > 3 > 2 > 4
1) CH3CHO 2) CH2 = CH2
3) CH3 – O – CH3 4) CH3 – CH3

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY
14. Correct reactivity order of E.S.R
18. Which of the following is the most correct
electron displacement for a nucleophilic
reaction to take place?

1) i > ii > iii 2) iii > ii > i

3) iii > i > ii 4) ii > i > iii
15. Most reactive towards E.S.R
1) Benzene 2) Chloro Benzene
3) Phenyl Acetate 4) Nitro Benzene 19. Which of the following singlet carbene is
16. Consider the following reaction most stable
•• ••
1) C H 2 2) C F2
•• ••
3) C Cl2 4) C Br2
20. Which of the following is incorrect about
dehydro halogenetion
ethanolic KOH
1) CH 3 − CH 2 − CH 2 − CH 2Cl  →
Which of the following base will give the CH 3 − CH 2 − CH = CH 2
− +
CH 3O K
best yield of the alkene II as the major 2) CH 3 − CH 2 − CH 2 − CH 2Cl  →
product – CH 3 − CH 2 − CH = CH 2
1) Alc.KOH 2) C2H5O- (CH )
3 3 CO −
3) (CH3)3CO -
4) MaNH2 3) CH 3 − CH 2 − CH 2 − CH 2Cl  →
CH 3 − CH 2 − CH = CH 2
17. Which of the following is not the product of
dehydration of CH 3
|
(CH3 )2 CO − K +
4) CH 3 − C − CHCl − CH 3 
( or ) Ethanolic KOH
→
|
CH 3
( CH 3 )3 C − CH = CH 2

21.

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY
22. The correct statement regarding −
4) I > Cl > Br > F
− − −
electrophile is 29. Arrange the following nucleophiles in the
1) Electrophile can be either neutralor order of their nucleophilic strength:
positively charged species and can form a
1) OH − > CH 3COO − > − OCH 3 > C6 H 5O −
bond by accepting a pair of electrons from a
nucleophile 2) CH 3COO − < C6 H 5O − < − OCH 3 < OH −
2) Electrophile a negativity charged species
3) C6 H 5O − < CH 3COO − < CH 3O − < OH −
and can form a bond by accepting a pair of
electron from anucleophile 4) CH 3COO − < C6 H 5O − < OH − < CH 3O −
3) Electrophile is a negatively charged species − − −
30. The nucleophilicities of CH 3 , NH 2 , OH
and can form a bond by accepting a pair of
−
electrons from another electrophile and F decrease in the order:
4) Electrophile are generally neutral species − − − −
1) CH 3 > NH 2 > OH > F
and can form a bond by accepting a pair of − − − −
electrons from anuleophile. 2) OH > NH 2 > CH 3 > F
23. Which of the following has the most − −
3) NH 2 > OH > CH 3 > F
− −
nucleophilicity? − − − −
4) CH 3 > OH > F > NH 2
31. Which of the following is the strongest
nucleophile?
−
1) OH 2) CH 3OH
− −
3) CH 3 S 4) CH 3O
32. Consider the following species:
Θ Θ

24. (a) CH2 = CH – CH = CH2 a) O H b) CH 3 − O

Θ Θ
(b) CH3 – CH = CH2
c) C H 3 d) N H 2
(c) CH3 – CH3
C – C single bond distance would be: Arrange these nucleophilic species in their
1) a (146 pm) b (151 pm) c (153 pm) decreasing order of nucleophilicity:
2) a (151 pm) b (146 pm) c (153 pm) 1) c > d > b > a 2) b > a > c > d
3) a (146 pm) b (153 pm) c (151 pm) 3) a > b > c > d 4) c > a > b > d
4) a (153 pm) b (146 pm) c (151 pm) 33. Which statement is correct for electromeric
25. Which of the following carbonyl compound effect?
is the least reactive towards N.A.R? 1) It is a temporary effect
1) C6H5CHO 2) CH3CHO 2) It is the property of π bond
3) C6H5COCH3 4) C6H5COC6H5 3) It takes place in presence of reagent, i.e.,
26. In which of the following – Cl is not electrophile or nucleophile
replaceable? 4) All are correct
1) CH3Cl 2) H2 = CH – CH2Cl 34. Which of the following exhibitelectromeric
effect?
1) Alkanes 2) Aldehydes
3) Alkyl halides 4) Alkyl amines
3) C6H5CH2Cl 4) 35. Shifting of electron of a multiple bond
27. The dipole moment of vinyl chloride is under the influence of a reagent is called
lower than that of methyl chloride. This is 1) I – effect 2) M – effect
due to: 3) E – effect 4) R – effect
1) Resonance effect 2) Inductive effect 36. Which among the following is wrong
3) Electromeric effect 4) Hyperconjugation electromeric effect?
28. Correct order of leaving group tendency:
− − − −
1) I > Br > Cl > F
− − − − 1)
2) F > Cl > Br > I ⊕ ⊕
− − − − 2) CH 3 − CH = CH 2 → CH 3 − C H − C H 2
3) Cl > F > Br > I

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY
⊕ 41. The order of reactivity of the following
3) −C ≡ N → C = N alcohols towards concentrated HCl is
⊕
4) CH ≡ CH → C H = C H
37. Which of the following molecule has the
longest C = C bond length?
1) CH 2 = C = CH 2
2) CH 3 − CH = CH 2
CH 3
|
3) CH 3 − C − CH = CH 2
|
CH 3
CH 3 − C = CH 2
4) | 1) I > II > III > IV 2) I > III > II > IV
CH 3 3) IV > III > II > I 4) IV > III > I > II
38. Consider the following three halides: 42. Which of the following species is attacked
a) CH3 – CH2 – Cl b) CH2 = CH – Cl by benzene in the electrophilic nitration
c) C6H5 – Cl reaction?
Arrange C – Cl bond length of these 1) NO+ 2) NO2
+
compounds in decreasing order: 3) NO2 4) HNO3
1) a > b > c 2) a > c > b 43. Which of the following compounds is least
3) c > b > a 4) b > c > a reactive in the nucleophilic aromatic
39. Reactivity of C – H bond (abstraction of H) substitution reaction with NaOH?
CH 3 = CH − H CH 3 − H 1) m – nitrochlorobenzene
(I ) ( II ) 2) o – nitrochlorobenzene
3) p – nitrochlorobenzene
CH 3CH 2 − H ( CH 3 )2 CH − H 4) 2, 4 – dinitrochlorobenzene
( III ) ( IV )
44. Which of the following is the strongest
( CH 3 )3 C − H activating group in electrophillic aromatic
(V ) substitution reactions?
1) II < III < I < IV < V 1) − N ( CH 3 )2 2) − NO2
2) I > II > III > IV > V
3) I < II < III < IV < V 3) −CO2CH 3 4) −OCH 3
4) I < II < IV < III < V 45. Among the following the strongest
40. Different hydrogen in nucleophiles is
a b b c d e f 1) C2H5SH 2) CH3COO-
CH 3 CH = CH − CH 2 − CH 2 − CH ( CH 3 )2 3) CH3NH2 4) NCCH2-
are represented by alphabets. Arrange 46. The reaction of HBr with
them in decreasing order of reactivity CH 3
towards radical substitution: | in the presence of
1) c > a > e > d > f > b CH 3 − C = CH 2
2) f > b > a > c > d > e peroxide will give
3) b > c > a > f > d > e
CH 3CBrCH 3
4) a > b > c > d > e > f
1) |
CH 3
2) CH 3CH 2CH 2CH 2 Br
CH 3
3) |
CH 3CHCH 2 Br

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY

CH 3 CH 3 − CH − CH 2 − CH 2OH
4) | 4) |
CH 3CH 2CHCH 3 OH
47. Which of the following compounds will 53. The increasing order of the rate of HCN
undergo Friedel-Crafts alkylation with addition to compounds A – D is
(CH3)3CCl, AlCl3 most rapidly? 1) HCHO 2) CH3COCH3
1) Acetophenone 2) Iodobenzene 3) PhCOCH3 4) PhCOPh
3) Toluene 54. Reaction of trans-2-phenyl-1-
4) Benzenesulphonic acid bromocyclopentane on reaction with
48. 3-phenylpropene on reaction with HBr alcoholic KOH produces
gives (as a major product) 1) 4-phenylcyclopentene
1) C6 H 5CH 2CH ( Br ) CH 3 2) 2-phenylcyclopentene
3) 1-phenylcyclopentene
2) C6 H 5CH ( Br ) CH 2CH 3 4) 3-phenylcyclopentene
3) C6 H 5CH 2CH 2CH 2 Br 55. Which of the following is the major
product of the following reaction?
4) C6 H 5CH ( Br )CH = CH 2
49. 2-methylbutane on reacting with bromine
in the presence of sunlight gives mainly
1) 1- bromo -2 – methylbutane
2) 2- bromo -2 – methylbutane 1) 2-bromo-2-methylpentane
3) 2- bromo -3 – methylbutane 2) 1-bromo-2-methylpentane
4) 1- bromo -3 – methylbutane 3) 4-bromo-2-methylpentane
50. Which of the following is most likely to 4) 3-bromo-2-methylpentane
undergo a favourable hydride shift? 56. Which of the following will undergo
dehydration most rapidly?

57. Consider the dehydration of

51. Elimination of bromine from 2-methyl-1-propanol.Which of the
2 – bromobutane results in the formation following carbocations results when a
of: hydride shift occurs in this mechanism?
1) Equimolar mixture of 1 and 2 – butane +
1) ( CH 3 )2 C CH 3
2) Predominantly 2 – butane
+
3) Predominantly 1 – butane 2) CH 3CH 2CH CH 3
4) Predominantly 2 – butyne +
3) ( CH 3 )2 CHCH 2
52. The major product formed in the following
reaction is 4) None of these
aq . KOH
CH 3CH ( Cl ) CH 2 − CH 2OH 
→
1) CH 3CH = CH − CH 2OH
2) CH 2 = CH − CH 2 − CH 2OH
CH 3 − CH − CH 2
3) | |
O − CH 2

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY
58.

The product are Electrotromeric effect, Nucleophilicity and types of

organic reactions
1 2 3 4 5 6 7 8 9 10
3 3 2 4 3 4 1 1 2 1
11 12 13 14 15 16 17 18 19 20
3 3 2 3 3 3 4 2 2 2
21 22 23 24 25 26 27 28 29 30
2 1 2 1 4 4 1 1 4 1
59. When 1-cyclohexlethanol is treated with
concentrated aqueous HBr, the major 31 32 33 34 35 36 37 38 39 40
product is
3 1 4 2 3 3 4 1 3 1
41 42 43 44 45 46 47 48 49 50
3 3 1 1 1 3 3 2 2 4
51 52 53 54 55 56 57 58 59 60
2 4 3 3 1 1 1 4 2 1
61
1

60. Dehydrobromination (-HBr) of the

following in increasing order is

1) 1 < 2 < 3 2) 3 < 2 < 1

3) 1 = 3 < 1 4) 3 < 1 < 2
61. Arrange the following compounds in the
order of increasing tendency to undergo
electrophilic substitution
1) Nitrobenzene 2) Benzene
3) Phenol 4) Toluene
5) Trimethyl phenyl ammonium ion
1) 5 < 1 < 2 < 4 < 3 2) 3 > 2 > 2 > 4 > 5
3) 1 > 2 > 5 > 3 > 4 4) 5 < 2 < 4 < 1 < 3

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TOPIC: Electromeric effect, Nucleophilicity and types of Organic reactions SUBJECT: CHEMISTRY

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