PRE-MEDICAL

ORGANIC
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ENTHUSIAST | LEADER | ACHIEVER

EXERCISE
Fundamental concepts in organic
reaction mechanism
ENGLISH MEDIUM
 TEAM ELECTRON
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Chemistry : Fundamental concepts in organic reaction mechanism ®
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EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ATTACKING REAGENT I-EFFECT

1. Which of the following species is an electrophile Θ

7. CH3 is less stable than :-
(1) RNH2 (2) SO3
Θ Θ
(3) NO3 (4) ROH (1) CH3— CH2
GC0001
Θ
(2) CH3— CH —CH3
2. Which of the following acts as a nucleophile?
⊕ Θ
(1) N O2 (2) :CCl2 (3) CH2 —NO2
Θ Θ
(3) N H2 (4) • CH3 (4) CH3— CH —C2H5
GC0002 GC0005

®
REACTION INTERMEDIATES 8. Decreasing order of –I effect of the triad
⊕
3. Which of the following contains only three pair [–NO2, – N H3 , –CN] is :-
of electrons : ⊕
(1) – N H3 > –NO2 > –CN
(1) Carbanion (2) Carbocation
⊕
(3) Carbon free radical (4) None (2) – N H3 > –CN > NO2
GC0003 ⊕
(3) –CN > –NO2 > – N H3
4. Carbanion is a :- ⊕

(1) Base (4) –NO2 > –CN > – N H3

(2) Nucleophile GC0006
(3) Both the above
(4) None 9. Most stable carbanion is :-
Θ Θ
GC0004 (1) HC ≡ C (2) H2 C = CH


5. In which structure carbon does not act as a CH3

electrophile.
(3) CH3–C–CH2 (4) CH3–C=CH
(1) CH3–CH2–Cl
CH3 CH3
(2) CH3–CO–CH3
GC0007
(3)
10. The correct order of stability of given carbanions
(4) CH3–CN will be :-
GC0160 CH3–CH2 CH2=CH HC≡C
6. Wrong statement regarding methyl carbonium (I) (II) (III)
⊕ (1) I > II > III (2) III > II > I
ion (C H3 ) .
(3) I > III > II (4) II > I > III
2
(1) It is sp hybridised GC0008
2
(2) Vacant orbital is sp hybridised
11. Which is most basic among the following :-
(3) Vacant orbital is perpendicular to molecular
planar and in pure p-orbital (1) CH3NH2 (2) CH3CH2NH2
(4) It is electrophile with sextet of electron (3) NH3 (4) (CH3)2CHNH2

GC0161 GC0009

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12. Which of the following has maximum pKa :- 20. Arrange the following in the acidic strength
(1) CH2FCOOH (2) CH2ClCOOH order :
(3) CH3COOH (4) HCOOH (a) NO2CH2COOH (b) NC–CH2COOH
(c) CCl3COOH (d) CHCl2COOH
GC0010 (1) a > b > c > d (2) c > d > a > b
(3) b > a > d > c (4) c > a > b > d
13. Which of the following is most acidic ? GC0163
(1) Methoxy acetic acid (2) Acetic acid
(3) Chloro acetic acid (4) Trifluoroacetic acid R- OR M-EFFECT
GC0011 21. Most stable carbocation is :-
⊕ ⊕
14. Which of the following show + I-effect :- CH2 CH2
(1) – OH (2) – OCH3 (3) – CH3 (4) – Cl
(1) (2)
GC0012

15. Among the following the most easily ionised in Cl NO2

⊕

®
water is: CH2
⊕
CH2
(1) CH3CH2CHClCOOH
(2) CH3CH2CCl2COOH (3) (4)
(3) CH3CHClCH2COOH
(4) CH2ClCH2CH2COOH OCH3
GC0013 GC0017

16. The strongest acid amongst the following 22. Most acidic compound is :-
compounds is ?
(1) CH 3CH 2CH(Cl)CO 2H (1) OH
(2) ClCH 2CH 2CH 2COOH
(3) CH 3COOH (2) CO2H
(4) HCOOH
GC0014 (3) H3C CO2H

17. Which of the following acids is stronger than (4) O2N CO2H
acetic acid :-
GC0018
(1) Propanoic acid (2) Formic acid
(3) Butyric acid (4) Iso butyric acid
23. Which resonating structure of vinyl chloride is
GC0015
least stable :-

18. Which of the following acids have the lowest pKa (1) CH2=CH– Cl :

value :- Θ ⊕

Cl (2) CH2 –CH= Cl

Θ ⊕
(1) CH3–CH–COOH (3) CH2 – CH –Cl
(2) Cl–CH2–CH2–COOH (4) All have equal stability
(3) CCl3COOH
GC0019
(4) CHCl2COOH
GC0016 24. The stabilization due to resonance is maximum in
19. In which σ bond, the inductive effect is
minimum? (1) (2)
C–C–C–C–Cl
(d) (c) (b) (a) (3) (4)
(1) a (2) b (3) c (4) d
GC0162 GC0020
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Chemistry : Fundamental concepts in organic reaction mechanism ®
is most stable
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25. In which of the following compounds 29. Which of the following
carbon-chlorine bond distance is minimum :- carbocation:-
(1) CH3–Cl ⊕
(1) (2) ⊕
(2) C6H5–CH2–Cl
⊕ ⊕
(3) CH2=CH–Cl (3) CH2 =
(4) CH CH − CH2
2
(4) CH2=CH–CH2–Cl
GC0021 GC0026

26. Consider the following carbocations 30. The oxygen atom in phenol –

⊕ (1) exhibits only inductive effect

⊕
(a) CH3O CH2 (b) CH2 (2) exhibits only resonance effect
(3) has more dominating resonance effect than
⊕ ⊕
(c) CH3 CH2 (d) CH3 − CH2 inductive effect

®
(4) has more dominating inductive effect than
The relative stabilities of these carbocations are
resonance effect
such that :-
GC0027
(1) d < b < c < a (2) b < d < c < a
(3) d < b < a < c (4) b < d < a < c 31. Which is incorrect stability order :-
GC0022 ⊕ ⊕
(1) CH2=CH– CH2 > CH3– CH –CH3
27. Arrange in decreasing order of basic strength : ⊕ ⊕
(2) CH2= CH < CH3– CH2
NH2 Θ Θ
NH2 (3) CH3 − CH2 − CH2 > CH3 − CH− CH3
(I) (II) ⊕ ⊕
(4) CH3– CH2 > CH3O– CH2
NO2 GC0028
NH2 NH2
32. Mesomeric effect is due to :-
(III) (IV) (1) Delocalization of σ es
(2) Delocalization of π es
CHO CH3
(3) Migration of H – atom
(1) I > II > III > IV (2) II > III > I > IV
(4) Migration of proton
(3) IV > I > III > II (4) IV > I > II > III
GC0029
GC0024
33. Among the following the pKa is minimum for :–
28. The most stable carbanion among the following
(1) C6H5OH (2) HCOOH
is
(3) C2H5OH (4) CH3C≡CH
CH2–CH2 CH2 GC0031
(1) (2)
34. Among the following the aromatic compound is–
CH2 CH2 (1) (2)
⊕
(3) (4)

OCH3 NO2 (3) (4)

GC0025 GC0032

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35. Which is aromatic among the following 40. Which of the following is most acidic :-
⊕ (1) phenol
(1) (2)
(2) benzyl alcohol
(3) m-chloro phenol
(3) (4) All the above
N (4) cyclohexanol
GC0039
GC0033

36. Select the correct option for stability of following 41. Which of the following is the strongest base :-

carbanions : (1) NH2 (2) NH–CH3

CH3
Θ Θ
CH3 ; C6 H5 CH2 ; CH3–C (3) NH2 (4) CH2–NH2
(I) (II) CH3 CH3

®
(III)
GC0040
(1) I > II > III (2) II > I > III
(3) III > II > I (4) II > III > I 42. The least carbon-chlorine bond length present
GC0034 in–
(1) Methyl chloride
37. The non aromatic compound among the
(2) Allyl chloride
following is :-
(3) Ethyl chloride
(1) (2) (4) Vinyl chloride
S
GC0410
(3) (4)
43. Which one of the following resonating structures
GC0036 of 1–methoxy–1,3–butadiene is least stable :–
Θ ⊕
38. The correct order of acidic strength of the (1) CH2 –CH=CH–CH= O–CH3
following compounds is :- Θ ⊕
(2) CH2=CH– CH2 –CH= O –CH3
A. Acetylene B. Ammonia
Θ ⊕
C. Phenol D. Carbonic acid (3) CH2– CH–CH=CH–O–CH3
(1) C > B > A > D (2) D > C > A > B
(4) CH2=CH–CH=CH–O–CH3
(3) B > D > A > C (4) A > B > D > C
GC0046
GC0409
44. Four structures are given in options (a) to (d).
39. Which one of the following compounds is most
Examine them and select the aromatic structures.
acidic:-
OH OH (a) + (b)
(1) (2)
NO2 CH3 (c) (d) –

OH (1) a and d (2) b and c

(3) (4) ClCH2CH2OH
(3) a and b (4) a and c
GC0047
GC0038

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Chemistry : Fundamental concepts in organic reaction mechanism ®
 is :-
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45. Order of acidic strength of the following 49. Decreasing order of basic strength
compound will be : NH2 NH2
OH OH
(1) Ph–NH2 > >
(A) (B)
CH3 NO2
Cl
CH3 NH2 NH2 NH2

OH OH (2) > >

(C) (D) CH3 NO2

COOH
SO3H NH2 NH2 NH2

(1) C > D > B > A (3) > >

(2) D > C > B > A
NO2 CH3

®
(3) A > B > C > D
(4) B > A > C > D NH2 NH2 NH2
GC0411
(4) > >
46. Phenol is less acidic than
CH3 NO2
(1) Ethanol
(2) o-Nitrophenol GC0166

(3) o-Methylphenol 50. Phenol are ortho para directing due to :

(4) o-Methoxyphenol (1) —OH groups shows +M & –I
GC0049 (2) —OH does not show hinderance
47. Temporary electron displacement effect in a (3) The resonance effect increases the e– density
molecule that occurs when a reagent approaches at o & p position
to attack if, is called as - –
(4) The I-effect decreases the e density at meta
(1) Inductive effect position
(2) Resonance effect GC0167
(3) Mesomeric effect 51. Which of the following is not aromatic ?
(4) Polarisability effect
(1) (2)
GC0164
48. Which statement is incorrect.
⊕
(1) The energy of actual structure of the
(3) (4)
molecule is lower than that of any canonical
structure GC0168
(2) The energy difference between actual 52. Arrange the following in their acidic strength
structure and least energy resonance order
structure is called as resonance energy H
(3) More number of resonating structure, more CH3–CH2–CH2–H H–C≡C–H
resonance (a) (b) (c)
(4) In equivalent resonance structure of acetate
(1) a > b > c (2) c > a > b
ion of C=O bond length are unequal
(3) b > a > c (4) a > c > b
GC0165 GC0169
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HYPERCONJUGATION TAUTOMERISM

53. Which of the following compounds exhibits 56. Which of the following will lead to maximum
hyperconjugation : enolisation :–
(1) Phenol (2) Ethyne O
(3) Ethanol (4) Propene (1) CH3–C–CH3
GC0051
(2) CH3–C–CH2–C–H
54. Which of the following is least stable :–
⊕ ⊕ O O
(1) CH3 − CH− CH3 (2) CH3 − CH2 − CH2
(3) CH3–C–CH–C– CH3
CH3
⊕ ⊕ O Br O
(3) CH3–C–CH3 (4) CH3–C–CH–C6H5
O
CH3 CH3 (4)
GC0052
GC0056
55. Which of the following is most stable alkene :-

®
H2N–C–NH2
H H 57. Urea molecule exhibits
(1) C=C O
H H (isomerism):-
CH3 H (1) Chain (2) Position
(2) C=C (3) Geometrical (4) Tautomerism
H H GC0057
H5C2 H
(3) C=C 58. Tautomerism is not observed in :–
H H (1) CH3–C–CH3 (2) Ph–CH=CH–OH
CH3 O
CH H CH3
(4) CH3 C=C
H H (3) CH3–NO2 (4) CH3–C–CHO
GC0053 CH3
GC0058

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 3 2 3 3 2 3 1 1 2 4 3 4 3 2
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 1 2 3 4 2 3 4 3 4 3 1 3 4 1 3
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 4 2 2 3 4 2 1 2 1 3 4 4 3 4 1
Que. 46 47 48 49 50 51 52 53 54 55 56 57 58
Ans. 2 4 4 2 3 4 2 4 2 2 4 4 4

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EXERCISE-II (Previous Year Questions) AIPMT/NEET
AIPMT 2015 Re-AIPMT 2015
1. In which of the following compounds, C–Cl bond
5. Which of the following statements is not correct
ionisation shall give most stable carbonium ion?
for a nucleophile ?
H
H3C CH–Cl
(1) Nucleophiles attack low e– density sites
(1) C–Cl (2)
H3C (2) Nucleophiles are not electron seeking
CH3
H (3) Nucleophile is a Lewis acid
C–Cl H3C H
(3) (4) C–Cl
O2NH2C H (4) Ammonia is a nucleophile
H3C
GC0080 GC0085
6. Correct order of Kb is
2. Consider the following compounds CH2NH2 NH2

®
CH3 Ph
(i) (ii)
CH3–C–CH– Ph–C–Ph
CH3 CH3 (iii) CH3CH2–NH2 (iv) H3C–C–NH2
O
(I) (II) (III)
(1) iv > iii > ii > i
Hyperconjugation occurs In :-
(2) iii > i > ii > iv
(1) II only (2) III only (3) I and III (4) I only
(3) i > ii > iii > iv
GC0081
(4) ii > iii > iv > i
3. Given :-
GC0086
H3C CH3 H3C CH2 H2C CH2
NEET-I 2016

7. The correct statement regarding a carbonyl

CH3 CH3 CH2 compound with a hydrogen atom on its
(I) (II) (III) alpha carbon,is :-
(1) a carbonyl compound with a hydrogen atom
The enthalpy of the hydrogenation of these
on its alpha-carbon never equilibrates with its
compounds will be in the order as :-
corresponding enol.
(1) III > II > I (2) II > III > I (2) a carbonyl compound with a hydrogen atom
(3) II > I > III (4) I > II > III on its alpha-carbon rapidly equilibrates with
GC0082 its corresponding enol and this process is
known as aldehyde-ketone equilibration.
4. Which of the given compounds can exhibit
(3) a carbonyl compound with a hydrogen atom
tautomerism?
on its alpha-carbon rapidly equilibrates with
CH3 CH3
CH3 its corresponding enol and this process is
CH3 CH3 known as carbonylation.
CH3 (4) a carbonyl compound with a hydrogen atom
O O O on its alpha-carbon rapidly equilibrates with
(I) (II) (III) its corresponding enol and this process is
(1) I and III (2) II and III known as keto-enol tautomerism.
(3) I, II and III (4) I and II GC0089
GC0083
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8. The correct statement regarding the basicity of NEET(UG) 2017
arylamines is :- 11. Which one is the correct order of acidity ?
(1) Arylamines are generally less basic than
(1) CH≡CH>CH3–C≡CH>CH2=CH2>CH3–CH3
alkylamines because the nitrogen lone-pair
(2) CH≡CH>CH2=CH2>CH3–C≡CH>CH3–CH3
electrons are delocalized by interaction with
the aromatic ring π electron system. (3) CH3–CH3 >CH2=CH2>CH3–C≡CH>CH≡CH
(2) Arylamines are generally more basic than (4) CH2=CH2>CH3–CH=CH2>CH3–C≡CH>CH≡CH
alkylamines because the nitrogen lone-pair GC0094
electrons are not delocalized by interaction 12. Which one is the most acidic compound ?
with the aromatic ring π electron system. OH OH
(3) Arylamines are generally more basic than
alkylamines because of aryl group. (1) (2)
(4) Arylamines are generally more basic than
NO2

®
alkylamines, because the nitrongen atom in
arylamines is sp-hybridized. OH
OH
GC0090 O2N NO2
(3) (4)
NEET-II 2016
CH3
NO2
9. Which among the given molecules can exhibit
GC0095
tautomerism ?
13. The correct increasing order of basic strength
O O
for the following compounds is :
Ph
O NH2 NH2 NH2
Ph

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

(1) Both I and II NO2 CH3

(2) Both II and III
(1) III < I < II (2) III < II < I
(3) III only (3) II < I < III (4) II < III < I
(4) Both I and III GC0096
GC0092 14. The correct statement regarding electrophile is:-
10. The correct order of strengths of the carboxylic (1) Electrophile is a negatively charged species
acids and can form a bond by accepting a pair of
electrons from another electrophile
COOH COOH COOH (2) Electrophiles are generally neutral species
O and can form a bond by accepting a pair of
O
electrons from a nucleophile
I II III
(3) Electrophile can be either neutral or
is positively charged species and can form a
(1) III > II > I bond by accepting a pair of electrons from a
(2) II > I > III nucleophile
(4) Electrophile is a negatively charged species
(3) I > II > III
and can form a bond by accepting a pair of
(4) II > III > I
electrons from a nucleophile
GC0093 GC0097

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NEET(UG) 2018 NEET(UG) 2020 (COVID-19)
15. Which of the following is correct with respect to 20. Which of the following substituted phenols is the
–I effect of the substituents ? (R = alkyl) strongest acid?
OH
(1) – NH2 < – OR < – F
(2) –NR2 < – OR < – F (1)
(3) – NH2 > – OR > – F
NO2
(4) – NR2 > – OR > – F
OH
GC0101
(2)
NEET(UG) 2019
16. The correct order of the basic strength of OCH3
methyl substituted amines in aqueous solution is:- OH
(1) (CH3)2NH > CH3NH2 > (CH3)3N

®
(3)
(2) (CH3)3N>CH3NH2 > (CH3)2NH
(3) (CH3)3N>(CH3)2NH>CH3NH2 C2H5
(4) CH3NH2>(CH3)2NH > (CH3)3N OH
GC0170
(4)

17. The compound that is most difficult to protonate CH3

is:- GC0413
O O NEET (UG) 2021(Paper-2)
(1) H H (2) H C H
3 21. Which among the following statements are
O O correct?
(3) H C CH3 (4) Ph H
3  ••
(a) C F2 is more stable than C Cl2
GC0171
•• ••
NEET(UG) 2019 (ODISHA) (b) C Cl2 is more stable than C Br2
•
18. The most stable carbocation, among the ••
(c) Singlet C H2 is more stable than triplet C H2
following is :-
..
⊕
(d) Singlet C H2 has planar geometry
(1) (CH3 )3 C − CH− CH3
⊕ (1) (a), (b), (d) (2) (b), (c), (d)
(2) CH3 − CH2 − CH− CH2 − CH3 (3) (a), (b), (c) (4) only (a)
⊕
(3) CH3 − CH− CH2 − CH2 − CH3 GC0425
⊕ NH2 NH2
(4) CH3 − CH2 − CH2
H5C2 C2H5
GC0172
NEET(UG) 2020 22. H5C2 C2H5
19. A tertiary butyl carbocation is more stable than a NO2 NO2
secondary butyl carbocation because of which of (P) (Q)
the following ? (1) – NO2 in (P) has weaker inductive effect
(1) Hyperconjugation (2) – NO2 in (P) has stronger – M group
(2) –I effect of –CH3 groups (3) – NO2 in (Q) has stronger – M group
(3) +R effect of –CH3 groups
(4) – NO2 in (Q) has weaker – M group
(4) –R effect of –CH3 groups
GC0426
GC0412
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23. The most enolic form of 2,4-pentanedione is NEET(UG) 2022 (OVERSEAS)
OH O 26. The correct order of acid strength of the
(1) CH2=C–CH2–C–CH3 following molecules is
OH
OH O
(1) C2H5OH < H2O < CH3COOH <
(2) CH3–C=CH–C–CH3

(3) H2C=C — C=CH–CH3 OH

(2) C2H5OH < H2O < < CH3COOH
OH OH

(4) CH3–C = C= C–CH3 OH

OH OH (3) H2O < C2H5OH < < CH3COOH

GC0427
OH
NEET(UG) 2022 (4) H2O < < C2H5OH < CH3COOH

®
24. Which compound amongst the following is not
an aromatic compound ? GC0430
Re-NEET(UG) 2022
(1) (2) 27. Which of the following is the most stable
⊕ ⊕
carbocation?
⊕
(1) (2)
(3) (4) ⊕

(3) ⊕ (4)
GC0428 ⊕
25. Given below are two statements: GC0431
Statement I :
NEET(UG) 2023
The acidic strength of monosubstituted
28. Consider the following compounds/species:
nitrophenol is higher than phenol because of
electron withdrawing nitro group.
Statement II : (i) (ii)
o-nitrophenol, m-nitrophenol and p-nitrophenol
will have same acidic strength as they have one
nitro group attached to the phenolic ring. (iii) (iv)
In the light of the above statements, choose the
most appropriate answer from the options given (v) (vi)
below:
(1) Both Statement I and Statement II are
incorrect.
(2) Statement I is correct but Statement II is (vii)
incorrect.
(3) Statement I is incorrect but Statement II is
The number of compounds/species which obey
correct
Huckel's rule is ______.
(4) Both Statement I and Statement II are
(1) 6 (2) 2 (3) 5 (4) 4
correct
GC0432
GC0429

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NEET(UG) 2023 (Manipur) 30. Given below are two statements:
29. Which amongst the following compounds/ Statement I :
species is least basic ? In an organic compound, when inductive and
H2N H2N ⊕ electromeric effects operate in opposite
(1) C=O (2) C–OH directions, the inductive effect predominates.
H2N H2N
Statement II :
Hyperconjugation is observed in o-xylene.
H2N H2N ⊕
(3) C=NH (4) C=NH2 In the light of the above statements, choose the
H2N H2N correct answer from the options given below :
(1) Statement-I is true but Statement-II is
GC0433
false.
(2) Statement-I is false but Statement-II is

®
true.
(3) Both Statement-I and Statement-II are
true.
(4) Both Statement-I and Statement-II are
false.
GC0434

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 2 1 3 3 2 4 1 3 4 1 3 3 3 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 1 4 3 1 1 1 3 2 3 2 2 4 4 2 2

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EXERCISE-III (Analytical Questions) Master Your Understanding

1. Consider the following statements :- 5. Which is wrong electromeric effect :
⊕ ⊕ ⊕
(a) CH3 O C H2 is more stable than CH C H (1) C=O → C–O
3 2

⊕ ⊕ ⊕ Θ
(b) Me2 C H is more stable than CH3 CH2 C H2 (2) CH3–CH=CH2 → CH3 − CH− CH2
⊕ Θ ⊕
(c) CH2=CH– C H2 is more stable than (3) –C≡N → − C =
N
⊕ ⊕ Θ
CH3 CH2 C H2 (4) CH≡CH → CH = CH

⊕ ⊕ GC0118
(d) CH2= C H is more stable than CH3 C H2

of these statements :- 6. Tautomerism is exhibited by :-

®
(1) a and b are correct O
CH3 CH3 O
(2) c and d are correct (1) CH (2) CH3–CH2–N
3 CH3 O
(3) a, b and c are correct
(4) b, c and d are correct O CH=O
GC0108
(3) (4)

2. Which of the following carbon has most acidic

O
hydrogen.
GC0119
O
CH3–CH2–CH2–C–H 7. Identify the compound that exhibits
4 3 2 1
tautomerism:-
(1) C1–H (2) C2–H (1) 2-Pentanone (2) Phenol
(3) C3–H (4) C4–H (3) 2-Butene (4) Lactic acid
GC0109 GC0120

3.
3
Hydrogen attached to sp carbon in 8. Arrange the following in correct order of acidic
cyclopentadiene can be easily removed as what :- strength :
(1) Hydride ion (2) Hydrogen molecule
(I) CH3–NO2
(3) Proton (4) Hydrogen atom
(II) NO2–CH2–NO2
GC0116
(III) CH3–CH2–NO2
4. Which one is most stable free radical : (IV) NO2–CH–NO2
Me CH2 NO2

(1) (2) (1) IV > II > I > III

(2) IV > II > III > I
•
=
(3) CH 2 CH − CH2 (4) CH3–C–CH3 (3) III > I > II > IV
CH3 (4) III > I > IV > II
GC0117 GC0121

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Pre-Medical
9. The correct order of stability of following carbon 13. Which is an example of +E effect ?
free radical is :- H ⊕ ⊕
(1) C=C → C–C
•
•
(CH3 )3 C CH2 H
(1)
(2) CN
(2) C=O → C–O
• •
CH3 CH2 CH2 CH3 CN
(3) (4)
(3) CCl3–CH=CH2 → CCl3–CH–CH2
(1) 1 > 2 > 3 > 4 OH
OH
(2) 4 > 3 > 2 > 1
Cl Cl OH
(3) 2 > 3 > 1 > 4
(4) 2 > 1 > 3 > 4 (4) →
OH

GC0122

®
GC0174
10. Which of the following is the strongest acid :- 14. Hyper conjugation involves delocalisation of
(1) Carbolic acid except?
(2) Carbonic acid
(1) Electrons of C–H bond towards directly
(3) Picric acid
attached unsaturated system
(4) Acetic acid
(2) Electrons of C–H bond towards directly
GC0123
attached positively charged carbon

11. The correct order of acidic strength is :- (3) Electrons of C–H bond towards directly
attached having unpaired electron
(1) CH3COOH < HCN < H2O < C2H5OH
(4) Electrons of C–H bond towards directly
(2) CH3COOH > HCN > H2O > C2H5OH
attached negatively charged carbon
(3) HCN > CH3COOH > H2O > C2H5OH
GC0175
(4) CH3COOH > HCN > C2H5OH > H2O
15. Which cation have no resonance with lone pair
GC0125 ⊕ ⊕
12. The two contributing structure of vinyl alcohol (1) (2)
are: OCH3 O

⊕ ⊕ ⊕ ⊕
CH2–CH=OH ↔ CH2–CH–OH (3) (4)
I II NH NH

Correct statement is/are : GC0176

(1) I is more stable than II due to complete octet 16. Which bond is more polar in following pair
(2) II is more stable than I due to less covalent (a) CH3–Br > CH3–H
bond (b) CH3–NH2 < CH3–OH
(3) Both are less stable than CH2=CH–OH due (c) CH3–F > CH3–Cl
to polar nature
(1) a, c only (2) a, b, c
(4) 1 and 3 both
(3) a, b only (4) b,c only
GC0173
GC0177

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Pre-Medical
17. Arrange the following derivative of carboxylic is in the order of :-
acid in their increasing order of their acidity. (1) (d) > (b) > (c) >(a)

COOH COOH COOH (2) (a) >(c) >(b) >(d)

(3) (a) > (b) > (c) > (d)
(1) < <
(4) (b) > (c) > (d) >(a)

OCH3 NO2 GC0063

COOH COOH COOH 21. Basic strength of :-

Θ
(2) > > (a) H3 C − CH2
Θ
OCH3 NO2 (b) H2 C = CH and
Θ
COOH COOH COOH (c) HC ≡ C

®
(3) > < is in the order of:-
(1) (a) > (c )> (b) (2) (a) > (b) > (c)
OCH3 NO2 (3) (b )> (a) > (c) (4) (c) > (b) > (a)
COOH COOH COOH GC0064

(4) = < 22. Which one of the following compounds has the
most acidic nature ?
OCH3 NO2
OH
GC0178
CH CH2OH
18. Which of the following is more basic than aniline (1) (2)
(1) Diphenyl amine (2) Triphenyl amine
(3) OH (4) OH
(3) p-nitro aniline (4) Benzyl amine
GC0061
19. Which of the following presents the correct order GC0065

of the acidity in the given compounds :

23. Given are cyclohexanol (I), acetic acid (II), 2, 4,
(1) FCH2COOH > CH3COOH > BrCH2COOH
6-trinitrophenol (III) and phenol (IV). In these the
> ClCH2COOH
order of decreasing acidic character will be :-
(2) BrCH2COOH > ClCH2COOH > FCH2COOH
(1) III > IV > II > I (2) III > II > IV > I
> CH3COOH
(3) FCH2COOH > ClCH2COOH > BrCH2COOH (3) II > III > I > IV (4) II > III > IV > I

> CH3COOH GC0066

(4) CH3COOH > BrCH2COOH > ClCH2COOH
24. Among the following four compounds :-
> FCH2COOH
(a) phenol
GC0062 (b) methyl phenol
(c) metanitrophenol
20. The stability of carbanions in the following :-
(d) paranitrophenol,
Θ
The acidity order is :
(a) RC ≡ C (b)
(1) c > d > a > b (2) c > d > c > b
Θ Θ (3) b > a > c > d (4) d > c > a > b
(c) R 2 C = CH (d) R 3 C − CH2
GC0067

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Pre-Medical
25. Which of the following species is not electrophilic
28. The radical, CH2 is aromatic because it
in nature :-
⊕ ⊕ ⊕ has :-
(1) BH3 (2) H3O (3) NO2 (4) Cl (1) 6p–orbitals and 7 unpaired electrons
GC0068 (2) 6p–orbitals and 6 unpaired electrons
(3) 7p–orbitals and 6 unpaired electrons
26. Which of the following compounds is most
(4) 7p–orbitals and 7 unpaired electrons
basic ?
GC0075
(1) NH2 (2) O2N NH2
29. The order of stability of the following tautomeric
•• •• compounds is :-
(3) CH2NH2 (4) N–COCH3
OH O
H
CH2=C–CH2–C–CH3
GC0070 (I)

®
27. The correct order of decreasing acid strength of O O
trichloroacetic acid (A), trifluoroacetic acid (B), CH3–C–CH2–C–CH3
acetic acid (C) and formic acid (D) is : (II)
(1) A > B > C > D (2) A > C > B > D
(3) B > A > D > C (4) B > D > C > A OH O

GC0073 CH3–C=CH–C–CH3
(III)

(1) II > III > I (2) I > II > III

(3) III > II > I (4) II > I > III
GC0076

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 2 3 1 3 2 1,2 1 4 3 2 4 1 4 4
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29
Ans. 3 1 4 3 3 2 3 2 4 2 3 3 2 3

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