CPP GOC, ISOMERISM

REVISION-1 (MAINS & ADVANCED) ` KKP / MYP CEN TRE

SINGLE OPTION CORRECT TYPE
1. The following compound has 3 types of nitrogen notified as X, Y and Z. x
y NH2
Identify the most basic nitrogen
N
(A) X (B) Y
(C) Z (D) All are equally basic
N
z
H

2. 4 3
HO OH

1
OH
O O
OH
2
Which of these – OH groups is most acidic
1 2 3 4
(A) OH (B) OH (C) OH (D) OH
3. The stability of the following carbonations decreases in the order
+ + + +

(1) (2) (3) (4)

(A) 4 > 1 > 2 > 3 (B) 4 > 2 > 3 > 1 (C) 4 > 3 > 2 > 1 (D) 4 > 2 > 1 > 3
4. + -
N N

The most stable canonical structure of this molecule is

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

5. Arrange the following carbanions in the increasing order of stability

- -
_ CH2 CH2 -
CH2 CH2

NO2
(1) (2) (3) (4)

NO2 OCH3
(A) 4 > 2 > 3 > 1 (B) 4 > 3 > 2 > 1 (C) 4 > 1 > 2 > 3 (D) 4 > 2 > 1 > 3
6. Which of the following are reasonating structures of each other?
-
O O O O
_ _
(1) (2) (3) (4)
_
(A) 1, 2 (B) 2, 3 (C) 1, 2, 3 (D) 1, 2, 4
7. Rank the following compounds in order of increasing acidity
Cl CH3 NO2

(1) Cl OH (2) H3C OH (3) O 2N OH (4)

OH
Cl CH3 NO2
(A) 2 < 3 < 1 < 4 (B) 1 < 2 < 3 < 4 (C) 3 < 1 < 2 < 4 (D) 2 < 4 < 1 < 3
8. Which carbocation is the most stabilized?
+

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

+ +

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9. Which one of the following resonating structures of 1-methoxy-1, 3-butadiene is least stable?
- + - +
(A) CH2  CH  CH  CH  O CH3 (B) CH2  CH  CH CH  O CH2
- + - +
(C) CH2  CH  CH  CH  O  CH3 (D) CH2  CH  CH CH O  CH3

10. Which is dehydrated to a maximum extent using conc. H2SO4?

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

OH OH
OH

11. The order of effectiveness of o- and p- directing groups is

(A) OH > NR2 > NH.COCH3 > CH3 > Cl (B) OH > CI > CH3 > NR2 > NH.COCH3
(C) OH > NH.COCH3 > CI > NR2 > CH3 (D) OH > CH3 > NH.COCH3 > CI > NR2
12. Which of the following compounds is the strongest acid?
(A) m-methoxybenzoic acid (B) p-bromobenzoic acid
(C) p-nitrobenzoic acid (D) m-methylbenzoic acid
13. Here the major product for the reaction is?
H2SO4
=?


OH

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

14. Identify the correct order of reactivity in electrophilic substance reactions of the following compounds :
CH3 Cl NO2

(1) (2) (3) (4)

(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1 (C) 2 > 1 > 3 > 4 (D) 2 > 3 > 1 > 4
15. Which nitrogen atom in LSD is most basic?
O
1 3
H N C N(et) 2
2
N
CH3
(A) 1 (B) 3 (C) 2 (D) All are equally basic
16. Consider the acidity of the carboxylic acids
(1) PhCOOH (2) o-NO2C6H4COOH (3) p- NO2C6H4COOH (4) m- NO2C6H4COOH
Which of the following order is correct ?
(A) 1 > 2 > 3 > 4 (B) 2 > 4 > 3 > 1 (C) 2 > 4 > 1 > 3 (D) 2 > 3 > 4 > 1
17. In the following there are three carbon– O Their lengths are
x y z
oxygen bonds denoted by x, y and z : H3C C O CH3 in the order
(A) x = y = z (B) x < y < z (C) x < y = z (D) y < x < z
18. Select the more basic one from each pair
NH2 NH2
ONa
ONa
H3C
(A) & H3C (B) &
II CH3
I CH3
Cl CH3
I II
ONa ONa
NH2

NH
(C) & (D) &

I NO2
II I II
NO2

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

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 1 1
19. 1
2
These are the three canonical structures of
2
2
naphthalene, choose the correct statement
3 3 3
about them
4 4 4
(A) all C-C bond lengths are same (B) C1-C2 bond length is less than C2-C3
(C) C1-C2 bond length is more than C2-C3 (D) None
20. Identify the major contributor in following canonical structures.
H3C CH C N H3C CH C N
(a)
I II

(b) H3C CH CH CH NO 2 H3C CH CH CH NO 2

I II
NH2 NH2
(c) H3C CH2 C NH2 H3C CH2 C NH2
I II
(A) a – II, b – II, c – I (B) a – I, b – II, c – II
(C) a – II, b – II, c – II (D) a – I, b – I, c – II

INTEGER TYPE
CH3
How many of the following effects/factors can stabilize the given C
21. species
CH3
( –Ph stands for phenyl group)
H3C O

Hyperconjugation by –CH3 Inductive effect of –Ph group Resonance

Inductive effect of –CH3 Mesomeric effect of –OCH3 group Inductive effect of –OCH3

22. Total number of hyperconjugable  – hydrogens available in the following carbocation is :

CH2
C CH3

CH
23. The number of alcohol(s) possible with the formula C4H10O
2
24. The number of sp hybridised carbon(s) in the following structure is
O

Cl C O
H
C C
H CH3

25. The number of tertiary carbons in the molecule 3–ethyl–4,5,6–trimethylnonane

KEY
1. A 2. C 3. D 4. C 5. D
6. D 7. D 8. A 9. C 10. D
11. A 12. C 13. B 14. C 15. C
16. D 17. B 18. D 19. B 20. C
21. 3 22. 5 23. 4 24. 7 25. 8

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MORE THAN ONE CORRECT TYPE
1. In which of the following molecules positive charge is / are delocalized because of resonance?
+
+ Me Me NH2 NH
+ ..
(A) (B) C N (C) C (D) C
+
Me Me H2N NH2 H3N NH2

2. Which of the following is / are incorrect relation between given pairs?

O OH NH2 NH2

(A) (B)
= Tautomers = Resonance
_
R O R O
+ S S
-
R R
(C) + (D) = Resonance
O O = Tautomers
_ H H
H H

3. In which cases free energy may decrease. If there can be some intramolecular rearrangtement?
+ CH3
H3C CH CH2 + + +
(A) (B) H3C C CH CH3 (C) CH2 (D) CH2
CH3 CH3

4. Which of the following correctly represent the acidic strength of given acids?
OH OH

(A) H2O > CH3OH > C2H5OH (B) > > C2H5OH

NO2
(C) CH2FCOOH > CH2NO2COOH (D) CH3COOH > CH3CH2OH

5. Which of the alkenes are formed here?

OH H2SO4
?
heat
CH3
OH

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

CH3 CH3 CH3 CH2

6. Rank the following compounds in order of decreasing solubility in water.

(I) CH3CH2F (II) CH3CH2OH (III) CH3CH2Cl (IV) CH3OCH3
(A) I is more soluble than II (B) I is less soluble than II
(C) III is more soluble than IV (D) III is less soluble than IV

7. –NO2 group is acid–strengthening group; when present in para–position of phenol and benzoic acid. Which statement is
false about this ?
(A) It increases acidity of both to the same extent.
(B) It increases acidity of phenol more than that of benzoic acid.
(C) It increases acidity of benzoic acid more
(D) It does not increase acidity of any of the compound.

8. Resonance structures of a molecule should have

(A) identical arrangement of atoms (B) nearly the same energy
(C) the same no. of paired electrons (D) identical bonding

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Integer type
9. Number of compounds/species which are aromatic

H
CH 2 N
N

(I) (II) (IIi) (IV)

N
N O
H
H

CH2
(V) (VI) (VII) + (VIII)
N N N
H
H

+ H

(IX) (X) (XI) (XII)

Compound for Integer based question number 10 – 12

(II)
NH2 O
F CO2H

H3C
N N(I)
(III)
HN F
(IV)
CH3 CO2Me

10. In the structure of sparfloxacin which nitrogen atom is most basic (nitrogen’s number) ?

11. The number of rings in the given molecule which is/are “not” aromatic?

12. In the given molecule how many functional groups (except double bond) are present

13. The IUPAC name of the given compound is

x,y-dimethylpentanoylbromide, then the value of (x + y) is ? Br

14. How many among the following PAIRS can be tautomers.

CH3

(a) CH3  COCH3 & CH3 CH2CHO (b) & O O

H3C
O OH

&
(c) (d)
& O O
O OH
O O

15. How many of the following compound are non-aromatic?

(i) (ii)
(iii) (iv)
(v) (vi) (vii)

16. The no. of stereoisomers possible for CH2 = CH – CHBr – CH = CH2 are

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COMPREHENSION TYPE
PARAGRAPH-1
Electronic effects of a group affects the acidic and basic strength of compounds. Electron donors decreases the
acidity while electron acceptors increases the acidity. Apart from electronic effects steric effects of the groups also
affect the acidic and basic strength in few cases.
17. The most acidic hydrogen in the following compound is
HO
O O 4 O

HO C CH2 C C OH
1 3

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

18. Which of the following is more acidic than benzoic acid?

COOH COOH
COOH COOH

CH3
(A) (B) (C) (D)
CH3
CH3 OCH3

19. Which of the following compounds has most acidic hydrogen?

(A) 2, 4-pentanedione (B) Methyl-3-oxobutanoate
(C) 2, 5-hexanedione (D) Dimethylpropanedioate

PARAGRAPH-2
It has been observed that in cases of certain compounds or ions, no single electronic structure can explain all the properties of
compounds or ions. Hence, more than one electronic structures are required for explaining the properties of compounds or ions.
This phenomenon is known as Resonance and the various electronic structures are known as resonating structures. Resonance
has an important role in deciding the stability of ions or molecules and acid – base character of species.

20. Which among the following structures is most stable?

O O
(A) (B)
H3C CH CH C CH3 H3C CH CH C CH3

O O
(C) (D)
H3C CH CH C CH3 H3C CH CH C CH3

21. Which of the following resonating structures is the major contributor to the resonance hybrid?
 
+
CH3 – CH2 – CH – O CH3  CH3 – CH2 – CH = O CH3
 
(A) I (B) II
(C) Both have equal contributions (D) They are not resonating structures

22. Consider the following two carbocations:

+ +
(i) (C6H5)2 CH (ii) C6H5 CH2
Which of the following statements is correct?
(A) (i) is less stable than (ii) (B) (ii) is less stable than (i)
(C) (i) and (ii) are equally stable (D) the stabilities of A and B cannot be predicted

PARAGRAPH-3
One of the drugs used to treat acquired immune deficiency syndrome (AIDS) is commonly known as AZT and it has
the following structure. AZT stands for 3’–azido–3’–deoxythymidine. Answer the questions based on the structure.
O

CH3
HN

N
O

HO

CHO

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23. The number of different functional groups (excluding unsaturation) present in the compound is
(A) 4 (B) 3 (C) 5 (D) 7

24. Identify the correct statement

1. Can exhibit geometrical isomerism
2. Can exhibit functional isomerism
3. The highest priority functional group is ketone
(A) 1 and 2 (B) 1 and 3 (C) 2 and 3 (D) 1, 2 and 3

25. The number of asymmetric carbon atoms present in the compound is

(A) 5 (B) 4 (C) 7 (D) 3

Match the following;

26.
List – I (intermediate) List–II (stabilized by)
(A) 
(p) Resonance
H3C  CH CH3

(B) Ph CH CH3 (q) Inductive effect

(C) (r) Hyperconjugation

Ph CH CH3

(D) H2C = CH  CH  CH3


(s) Electrometric effect

27. Match the column– I with column – II.

Column– I Column– II
(A) A A A A (p) Enantiomers
C C C and C C C
B B B B

(B) Cl Cl
(q) Structural isomers
Cl

and
Cl

(C) Et CH3 Et (r) Same compound

Et
H C N Et and H C N CH3
Me CH(CH3)2 Me CH(CH3)2

(D) H3C Br H3C Br (s) Diastereomers

H and H H
H
Br CH3 Br CH3

28. Column – I Column – II

(A) Inductive effect (p) Delocalisation of  e 
(B) Electromeric effect (q) Displacement of  e 
(C) Resonance (r) -H-atom
(D) Hyperconjugation (s) Influence stability of carbocation
(t) Complete transfer of  e 

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29.
Column – I Column – II
(Pair of compounds) (Type of isomers)

(A) (P) Positional isomers

H3C CH3 H3C CH3

(B) & (Q) Identical structures

COOH COOH
O CH3 O CH3

(C) & (R) Enantiomers

(D) (S) Constitutional isomers

(T) Diasteromers

KEY

26. ABC 27. ABD 28. ABD 29. ABD 30. ABD

31. AD 32. ACD 33. ABC 34. 6 35. 4

36. 2 37. 6 38. 5 39. 2 40. 2

41. 0 42. B 43. A 44. A 45. A

46. B 47. B 48. C 49. A 50. D

26. Aq,r ; B pqr ; C p ; D pqr 27. A P, B q C p ; D r

28. A  Q, S ; B  T; C  P, S; D  P, R, S 29. A –Q ; B –T ; C –P ; D –S

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