1

ARJUNA (JEE)
DPP-01
Isomerism
1. Which one of the compounds shown below, O OH O
is not an isomer of the others?
4.
(A)
(I) (II) (III)
The tautomer of II is
(A) I (B) III
(B)
(C) Both I and III (D) None of these

O
(C)
H
5.
(D) H
H
In the enolization of the given molecule, the
2. Which of the following is an isomer of H- atom involved is :
compound 1 ?
(A)  – H
O
(B)  – H
CH3CH2CHO, CH3 – C – CH3 (C)  – H
(1) (2) (D) Cannot be enolized
CH3 – CH = CH – OH CH2 – CH – CH3
(3) O (4) O
(A) 2 (B) 4 O O
(C) 2 and 3 (D) all are isomrs 6.
O O
3. Which of the following substances is not an O
isomer of 3-ethyl 2-methyl pentane? (I) (II) (III)
Among the given structure which can exhibit
(A) tautomerism?
(A) I only (B) II only
(B) (C) III only (D) none of these

(C)

(D) All are isomers

 2

O O 9. Which of the following pairs of compounds

CH3 are functional isomers?
7. CH3 (A) and O
CH3
CH3 OH
(I) O O
(II)
(B) and
O O
CH3 CH3 OH O
(C) and
CH3 CH3

O
(III) O
(D) O and
Identify the which can exhibit tautomerism?
(A) I only (B) II only O
(C) III only (D) All of these

8. Which of the following pairs of compounds

are not positional isomers?

HO CH3 OH
(A) and
CH3
CH3
(B) and
CH3 OH OH

CH2OH OCH3
(C) and

(D) All of the above

 3

ANSWER KEY
1. (D)
2. (D)
3. (B)
4. (C)
5. (C)
6. (B)
7. (D)
8. (C)
9. (B)

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 1
ARJUNA (JEE)

Isomerism DPP-02

1. Number of structural isomers possible for 6. How many total structural isomers are
C4H10O are possible for alkyne with molecular formula
(A) 7 (B) 6 C6H10?
(C) 4 (D) 5 (A) 1 (B) 2
(C) 7 (D) 4
2. Number of structural isomers possible for
C4H8 are: 7. HCOOCH2CH3 and CH3CH2COOH are
(A) 3 (B) 4 related as
(C) 5 (D) 6 (A) Functional isomers only
(B) Functional and chain isomers
3. The type of isomerism due to different (C) Metamers only
types of alkyl group on either side of (D) Chain isomers
functional groups in the molecule of
compounds CH3CH2OCH2CH3 and 8. The number of ether metamers represented
CH3OC3H7 is referred as by molecular formula C4H10O is
(A) Metamerism (A) 1 (B) 2
(B) Chain isomerism (C) 3 (D) 4
(C) Functional isomerism
(D) Position isomerism 9. How many ketones (structural isomers) are
possible with molecular formula C6H12O?
4. Total number of structural isomers with (A) 5 (B) 6
molecular formula of C7H8O containing (C) 7 (D) 8
benzene is
(A) 3 (B) 4 10. How many structural isomers of C9H18 that
(C) 6 (D) 5 have a six membered ring and
trisubstituted?
5. Structural isomers possible for C4H8Br2 are (A) 3 (B) 4
(A) 6 (B) 9 (C) 5 (D) 6
(C) 10 (D) 4
 2
ARJUNA (JEE)
ANSWERS KEY
1. (A)
2. (C)
3. (A)
4. (D)
5. (B)
6. (C)
7. (A)
8. (C)
9. (B)
10. (D)

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 1

Arjuna (JEE)
DPP-03
ISOMERISM
1. Identify the compound with E configuration (C) CH3 – C = CH2 – CH3
|
CH3
(A)
(D) CH3 – CH – CH = CH – CH2 – CH3
|
CH3
(B)
5. Which of the following compounds will
exhibit cis-trans (geometrical) isomerism?
(C) (A) but-2-ene (B) Butanol
(C) but-2-yne (D) buten-2-ol

(D) 6. Which of the following compounds have Z-

configuration?

2. Identify the compound having trans

(A)
configuration.

(A) (B)

(C)
(B)

(D)
(C)
7. Which of the following can show
(D) None of these geometrical isomerism ?
(A) H3C CH = CH CH3
3. Which of the following does not show (B) PhCH = N(Ph)
geometrical isomerism? (C) (Ph) N = N (Ph)
(A) 1, 2 Dichloro pent-1-ene (D) All of the above
(B) 1, 3 Dichloro pent-2-ene 8. Choose the correct option from the
(C) 1, 1 Dichloro pent-1-ene following.
(D) 1, 4 Dichloro pent-2-ene (A) A group gets priority if its atomic
number is high
4. Which of the folloiwng will not show cis- (B) When atoms attached to a double bond
trans-ismerism? have same atomic number, the first
(A) CH3 – CH = CH – CH3 atoms are considered
(B) CH3 – CH2 – CH = CH – CH2 – CH3
 2

(C) A group gets priority if its atomic

number is low
(D) Lone pair gets more priority and is
ranked above hydrogen

9. The cis-trans nomenclature is not applicable

when _________.
(A) The different groups attached to the
carbon atom of double bond are same
(B) Atleast one of the group attached to
each carbon atom is same
(C) The different groups attached to the
carbon atom of double bond are not
same
(D) The cis-trans nomenclature is
applicable for all compounds
 3

ANSWERS KEY

1. (B)
2. (D) None of these
3. (C) 1, 1 Dichloro pent-1-ene
4. (C) CH3 – C = CH2 – CH3
|
CH3
5. (A) but-2-ene
6. (B)
7. (D) All of the above
8. (A)
9. (C)

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 1

Arjuna (JEE)
DPP-07
ISOMERISM
1. The configuration of the given compound 4. Which shows the same compound as the
is: following?
COOH
H NH2
CH3
(A) R (B) S (A) (B)
(C) E (D) Z

2. Which of the following has the (R) (C) (D)

configuration?

5. Which compound is the enantiomer of the

(A)
following?

(B)

(A)
(C)

(B)
(D)

(C)
3. Which of (a)-(d) shows the same compound
as the following?
(D)

6. Which of the following compounds is

achiral?
(A) (B)
(A) (B)

(C) (D) (C) (D)

 2

7. Which of the following has the (R) 9. Which of the following Fischer projections
configuration? is different from the other three?

(A) (B)

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

10. What is the molecular formula for the

8. Which of the following has the (S) alkane of smallest molecular weight which
configuration? possesses a stereogenic center?
(A) C4H10 (B) C5H12
(C) C6H14 (D) C7H16
(A) (B)

(C) (D)

.
 3

ANSWERS KEY

1. (A)
2. (A)
3. (D)
4. (C)
5. (C)
6. (C)
7. (B)
8. (D)
9. (C)
10. (D)

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 1

Arjuna (JEE)
DPP-09
ISOMERISM
1. Which of the following is the most stable 6. The potential energy of n-butane is
conformation of 1-bromopropane? maximum for ___________
(A) Skew conformations
(B) Staggered conformations
(C) Eclipsed conformations
(A) (B) (D) Gauche

7. In gauche conformations, the methyl groups

are ___________
(A) 60 apart (B) 90 apart
(C) 180 apart (D) 360 apart
(C) (D)
8. Which of the following is least stable?
(A) Anti conformation
(B) Gauche conformation
2. The dihedral angle between two C – H (C) Staggered conformation
bonds in the staggered conformation of (D) Eclipsed conformation
ethane is:
(A) 60 (B) 180 9. In the given conformation C2 is rotated
(C) 0 (D) 120 about C2 – C3 bond anticlockwise by an
angle of 120, then the conformation
3. The stable conformer of ethane-1, 2-diol is obtained is
(A) Gauche (B) Eclipsed C CH3
4
(C) Anti (D) None of these H H
4. The correct order of stability of conformers C3
is: C2
H H
(A) Staggered > Skew > Eclipsed C1
(B) Eclipsed > Skew > Staggered CH3
(C) Skew > Eclipsed > Staggered (A) Fully eclipsed conformation
(D) None of the above (B) Partially eclipsed conformation
(C) Gauche conformation
5. Conformations are different arrangements (D) Staggered conformation
of atoms that can be converted into one
another by rotation about ___________.
(A) Covalent bond (B) Double bond
(C) Single bond (D) Triple bond
 2

ANSWERS KEY

1. (A)
2. (A)
3. (A)
4. (A)
5. (C)
6. (C)
7. (A)
8. (D)
9. (C)

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 1

Arjuna (JEE)
DPP-08
ISOMERISM
1. Which of the following statements 5. Which of the following molecules exists as
regarding enantiomers not true? a pair of enantiomers?
(A) All (–) enantiomers are levorotatory (A) 2-Bromopropane
(B) All (–) enantiomers rotate plane (B) 1-Bromo-3-methylbutane
polarized light in a counterclockwise (C) 2-Cyclohexen-1-ol
direction
(D) cis-1,2-Dichlorocyclobutane
(C) (+) and (–) enantiomers rotate plane
polarized light in opposite directions 6. Which of the following is capable of
(D) All R enantiomers are dextrorotatory existing as a pair of enantiomers?
(A) 2-methylpropane
2. Which of the following is/are the S- (B) 2-methylpentane
enantiomer of alanine? (C) 3-methylpentane
(D) 3-methylhexane

7. Which is the correct assignment of chirality

at C2 and C4 of the following molecule?
(A) Only 1 (B) Only 2
(C) 1 and 3 (D) 2 and 3

3. The given compounds are:

CH2CH2CH3 (A) 2S,4S (B) 2R,4R
H
(C) 2S,4R (D) 2R,4S
H3C Cl H3C Cl
CH2CH2CH3 H 8. Which is the correct assignment of chirality
(A) Identical at C2 and C3 of the following molecule?
(B) Geometrical isomers (A) 2S, 3S
(C) Enantiomers (B) 2R, 3R
(D) None of these (C) 2S, 3R
(D) 2R, 3S
4. Is the given pair of compound enantiomers? 9. The configuration of the given compound at
C-2 and C-3 is:
CH3
H OH
(A) True (B) False H Br
(C) Both (D) None of these CH3
(A) S, R (B) R, R
(C) S, S (D) R, S
 2

10. Which of the following is the definition for

enatiomerism?
(A) A pair of stereoisomers each of which
has two chirality centres
(B) A pair of stereoisomers that are not
mirror images of one another
(C) A pair of stereoisomers that are non-
superimposable mirror images of one
another
(D) Any pair of stereoisomers .
 3

ANSWERS KEY

1. (D)
2. (C)
3. (C)
4. (A)
5. (C)
6. (D)
7. (B)
8. (D)
9. (A)
10. (C)

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 1

Arjuna (JEE)
DPP-05
ISOMERISM
1. The total number of geometrical isomers of 6. The other geometrical isomer of the given
the following compound are: compound is:
H H
C=C O
Cl
H O
Cl
(A) 2 (B) 4 H
H
(C) 6 (D) 8
O H
2. The number of structural and geometrical O O O
(A) (B)
isomers in dimethylcyclohexane are:
H H
(A) 3, 6 (B) 6, 4 H
(C) 4, 6 (D) 6, 3
O

3. The given compound represents (C) O (D) All of the above

H CH3 H
7. Which of the given compounds show
geometrical isomerism

(A) E-isomers
(B) Z-isomer
(C) R-configuration
(D) None of the above (1) (2) (3)
(A) Only 1 (B) Both 2 and 3
4. The total number of possible cycloalkanes (C) All 1, 2 and 3 (D) Both 1 and 2
with formula C5H10, which can show
geometrical isomers are: 8. Total number of geometrical isomers in the
given compound are:
(A) 1 (B) 2
(C) 3 (D) 4

NH
5. Does the given compound exhibits (A) 8 (B) 6
geometrical isomerism? (C) 4 (D) 10
C O O A
9. Find the total number of geometrical
D B
isomers:
(A) yes O
(B) No
(C) When A = C and B = D C
(D) When All A, B, C and D groups are (A) 8 (B) 6
different
(C) 4 (D) zero
 2

10. The number of geometrical isomers of the

given compound are:
CH3
H3C HC = C
H CH3 CH = CHCH3

(A) 2 (B) 6
(C) 8 (D) 4
 3

ANSWERS KEY

1. (B)
2. (C)
3. (B)
4. (A)
5. (B)
6. (C)
7. (B)
8. (C)
9. (D)
10. (C)

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 1

Arjuna (JEE)
DPP-06
ISOMERISM
1. Allegra, a common prescription drug with 4. How many chiral centers are in the
the structure shown below, is given for the following compound?
treatment of seasonal allergies. How many
stereo genic carbon does Allegra possess?

(A) 4 (B) 5
(C) 6 (D) 7

(A) 1 (B) 2 5. The structural formula of cocaine is shown

below. How many stereogenic carbon
(C) 3 (D) 4 atoms are there in this molecule?

2. The following molecule is fluorometholone,

a steroidal anti-inflammatory agent. How
many stereogenic centers does it contain?

(A) 1 (B) 2
(A) 5 (B) 6 (C) 3 (D) 4
(C) 7 (D) 8
6. The structural formula of sativene is shown
3. How many chiral carbons are there in below. How many stereogenic centers are
Reserpine (an antipsychotic drug)? there in this molecule?

(A) 9 (B) 8
(C) 7 (D) 6 (A) 2 (B) 3
(C) 4 (D) 5
 2

7. When does a chiral center occur? 9. A compound with one chiral carbon is
(A) when a carbon atom is connected to _______chiral.
four different atoms or groups of (A) Never
atoms (B) Always
(B) when a carbon atom is connected to (C) May be
three different atoms or groups of (D) None of the above
atoms
(C) when a baby is born with birth defects
10. Number of stereo centers in the given
(D) when molecules are identical to each compound are:
other
H
Ph
8. Shown above is the chemical structure for C
penicillin, a common prescription drug. Br
How many chiral carbons does penicillin
have? (A) 1 (B) 3
(C) 2 (D) 4

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

ANSWERS KEY

1. (A)
2. (D)
3. (B)
4. (C)
5. (D)
6. (D)
7. (A)
8. (C)
9. (B)
10. (B)

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 1

Arjuna (JEE)
DPP-04
ISOMERISM
1. How many cyclic isomers (structural and 6. The total number of geometrical isomers of
geometrical only) for C3H3Cl3? the given compound are:
(A) 2 (B) 3 H3C – CH = CH – N = N – HC = CH – CH3
(C) 4 (D) 5 (A) 8 (B) 3
(C) 6 (D) 4
2. Does the given compound show
geometrical isomerism?
7. The total number of geometrical isomers of
H H
the following compound is/are:
C=C=C
H3C CH3
(A) Yes CH – CH = CH – CH3
(B) No
(A) 2 (B) 4
(C) Not enough information (C) 3 (D) 6
(D) Only if side groups are different.
8. The given compound will show geometrical
3. Which double bond in the given compound
isomerism, if
will show geometrical isomerism?
(3)
D A
H3C H C B
C=C=C=C CH = CH2 (A) A and D are same
H C=C= (B) A and B are same
(1) H CH3
(2) (C) All are different
(A) 1, 2 and 3 (D) Never
(B) 2 and 3 only
(C) 1 only 9. The number of geometrical isomers
(D) None of the above possible for the given compound is/are
H3C CH3
4. In anti form of the given compound

N=C=N
H H
CH3 CH3
(A) Lone pairs are at opposite position (A) 3 (B) 4
(B) Hydrogen atoms are at opposite (C) 5 (D) 6
position
(C) Position of nitrogen is changed 10. The compound which will show
(D) Does not exist geometrical isomerism is:
H3C H
5. The total number of given compounds (A) C=C=C
which can exhibit geometrical isomerism H CH3
are/is: H CH3
(B)
H3C H
(C) H2C = CHCH3

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

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

ANSWERS KEY

1. (B)
2. (B)
3. (C)
4. (D)
5. (A)
6. (C)
7. (A)
8. (D)
9. (B)
10. (B)

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