DPP-1 Time: 20 Minutes

Q.1 Relationship between molecules:

(a) &

(b) &

(c) &

(d) CH2 OH & O CH3

(e) &

(f) &

(g) &
COOH
COOH

(h) OH &
OH

(i) &

H
(j) CH3 CH2 CH2 NH2 & 3 2

CH3

(k) O CH3 & CH2 OH

2
 OH 2

(l) CH3 &

(m) & CH3 C C CH3

CH3

(n) CH3 CH2 CH2 CH2 NH2 & CH 3 CH2 N

CH 3

O O

2 3
(o) &

(p) &

(q) &

(r) &

Q.2 Fill in the blanks:

O O
(a) & are _ _ _ _ _ _ _

(b) & are _ _ _ _ _ _ _

O O

(c) H & H are _ _ _ _ _ _ _

C=C C=C
CH3 H CH3 H

(d) CH3 CH2 CH2 N CH3 & CH3 CH2 N CH2 CH3 are _ _ _ _ _ _ _
| |
H H

(e) CH3 CH2 CH2 C N & CH3 CH2 CH2 N C are _ _ _ _ _ _ _

3
(f) CH2 SH & S CH3 are _ _ _ _ _ _ _

O O
||
(g) & CH3 CH2 C CH3 are _ _ _ _ _ _ _
3 2 2

H
O O
||
(h) 3 2 2 & CH3 CH2 C CH2 CH3 are _ _ _ _ _ _ _
CH3

Q.3 Column matching

Column I Column II
H
(A) & CH2 NH2 (P) metamers
CH3
O O
|| ||
(B) H C OCH3 & CH3 C OH (Q) functional isomers

(C) & (R) position

O
O
H
(D) C=C & H (S) identical
H H C=C
H H

4
DPP NO- 2 Time: 15 minutes
Compounds Relationship

1. &

O
2. &
O

3. &

4. &

Cl Br

5. &
Br Cl

6. CH2 = CH CH2 OH & CH2 = CH OCH3

O
O
7. &

O
8. 2 2 & 3 3

9. &

10. &

11. &

12. CH3OCH3 & CH3OCH2CH3

5
 Compounds Relationship

13. &

14. &
O CHO

SH
HS OH
15. &
OH

H CH3

16. &
Et H H H
CH3 Et

OH OH
17. &

OCH3
18. OCH3 &

CH3 CH2CH3
H Br H Br
19. &
H Cl H Cl
CH2CH3 CH3

CH3 Me

20. H Cl & Cl H

Me CH3

21. &

N
22. & N
H

6
DPP NO- 3 Time: 15 minutes
Q.1 Which of following is 2° alcohol ?
OH
(A) (B) (C) OH (D)
OH OH

Q.2 Which of following is 3° alcohol ?

OH OH

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

OH
OH

Q.3 Which of following is 2° amine ?

NH2
NH2 3

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

N
CH3

Q.4 Which of following compound has presence of 1°, 2°, 3°, 4° carbon ?

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

Q.5 How many ether is/are possible for molecular formula C4H10O.
(A) 1 (B) 2 (C) 3 (D) 4

Q.6 How many ketone is/are possible for molecular formula C4H8O
(A) 1 (B) 2 (C) 3 (D) 4

Q.7 How many alcohol is/are possible for Molecular farmula C4H10O (only structural)
(A) 2 (B) 3 (C) 4 (D) 5
O
Q.8
O
Number of Functional group in above compound is
(A) 3 (B) 4 (C) 5 (D) 6

7
Q.9 The functional groups in Cortisone are:
HOH2C
CH3 OCH3
O

O Cortisoe
(A) Ether, alkene, alcohol (B) Alcohol, ketone, alkene, ether
(C) Alcohol, ketone, amine (D) Ether, amine ketone

O
O

Q.10 H SH
OH OH
How mnay types of functional groups are presention given compound.
(A) 6 (B) 5 (C) 4 (D) 7

Q.11 The hybridization of carbon atom in the given compound

(A) sp2, sp (B) sp3, sp2 (C) sp3, sp (D) only sp2

Q.12 Bond X is made by the overlap of which type of hybridized orbitals?

X
3 2
(A) sp and sp (B) sp and sp (C) sp2 and sp3 (D) none of these

Q.13 The number of sp2 sp2 sigma bonds in the compound given below is:

(A) 1 (B) 3 (C) 4 (D) 5

Q.14 Present functional group is

CH3 O

O CH3
(A) ketone (B) ester (C) ether (D) alcohol

Q.15 Present functional group is/are

O O
OCCH3

O
(A) ketone (B) ester (C) ether (D) A and B both
8
Q.16 Find out the degree of carbon in the following compounds
CH3
(a) 3 2 2 2 2 3
(b)

3 2 3

4-ethyl-3-methyloctane

CH3 CH3
1,2,7-trimethylcyclopentadecane

CH3
CH3
(c) (d)
CH3

CH3 CH3
1,1,2,5-tetramethylcyclopentane

Q.17 Calculate DBE value of C4H8 and draw possible structural isomer

Q.18 Calculate C3H6O, DBE value & draw all possible structural isomer.

Q.19 Calculate DBE value of C5H10 & draw all possible structural isomer.

Q.20 Calculate DBE value of C4H6 and draw all the possible structural isomers.

Q.21 Calculate DBE value of C2H4O2 and draw all the possible structural isomers.

9
DPP NO- 4 Time: 15 minutes
Q.1 Identify relationship between following molecules.

(a) & (b) &

(c) & (d) &

(e) CH3 CH2 CH2 CN & CH3 CH CH3

|
CN

(f) & (g) &

(h) CH3 CH CH2 CH3 & CH3 CH2 CH2 CH2 OH

|
OH
NH2

(i) & (j) &

NH2

(k) &

Q.2 Calculate I.H.D. in the following molecules:

O CH2 NH 2
(a) (b) (c)

CH3

CH3 O O O
(d) Cl (e) H2N OH
O
Q.3 Calculate No. of & / bonds in the following molecules:

(a) (b) (c)

O=C OH
Cl
(d) (e) N C C N
O

CN
10
 O O
|| ||
(f) C H (g) C OH
| |
C H C OH
|| ||
O O

Q.4 Which of the following is the staggered conformation for rotation about the C1 C2 bond in the
following structure?
CH3
CH3CHCH2CH3
1 2 3 4
H CH3 H
CH3 CH2CH3 CH3 CH2CH3 CH3 CH3
(I) (II) (III)
H H CH3 H H H
H H H
H H
C2H5 H H

(IV) (V)
H H CH3 H H CH3
H
(A) I (B) II (C) III (D) IV and V

Q.5 Which of the Newman projections shown below represents the most stable conformation about the
C1 C2 bond of 1-iodo-2-methyl propane?
CH3 CH3 CH3 H
H CH3 I H I I CH3
H
(A) (B) (C) (D)
H H H H H CH3 H H
I CH3 H CH3

Q.6 Among the butane conformers, which occur at energy minima on a graph of potential energy versus
dihedral angle?
(A) gauche only (B) eclipsed and totally eclipsed
(C) gauche and anti (D) eclipsed only (E) anti only

Q.7 Which of the following best explains the reason for the relative stabilities of the conformers shown?
CH3 CH3
H H H CH3

(I) (II)
H H H H
CH3 H
(A) I has more torsional strain (B) I has more steric strain
(C) II has more torsional strain (D) II has more steric strain

Q.8 Draw the Newman projection that represents the least stable conformation of 3,3-dimethylhexane
viewed along the C3-C4 bond.

11
Q.9 Draw the Newman structure for the most stable conformation of 1-bromopropane considering
rotation about the C1 C2 bond.

Q.10 Draw a Newman projection of the most stable conformation of 2-methylpropane.

Q.11
(a) Write Newman projections for the gauche and anti conformations of 1,2-dichloroethane
(ClCH2CH2Cl)
(b) The measured dipole moment of ClCH2CH2Cl is 1.12 D. Which among the following statements
about 1,2-dichloroethane is/are false?
(1) It may exist entirely in the anti conformation.
(2) It may exist entirely in the gauche conformation.
(3) It may exist as a mixture of anti and gauche conformations.

CH3
H CH3
Q.12 ; If front carbon is rotated by 180° the conformation formed is:
H H
H
(A) gauche (B) anti (C) partially eclipsed (D) perfectly eclipsed

CH3
H CH3
Q.13 In the given energy diagram for butane the above conformation is represented at
H H
H
which point
D B

E
A
C
angle of rotation
(A) A (B) B (C) C (D) D

Q.14 If for 1,2-dibromoethane is 0.75 D and Xanti = 0.7 Calculate for gauche.

Q.15 Compare relative stabilities of given conformers.

CH3 CH3 CH3
H H CH3 CH3 H
H
(a) (b) (c)
H H H H H H
CH3 H H

Q.16 Draw most stable conformer of

(a) 3-methyl pentane
(b) 3-methyl hexane

Q.17 Draw most stable forms of

Z CH2 CH2 OH
O O
|| ||
Z = OH, F, Cl, NH2, OMe, C OH, C H

12
 O
||
Q.18 (Me3) N CH2 CH2 O C CH3; Most stable form of the compound.

Q.19 Draw most stable conformers of 3 2 2 & CH3 CH O H

|
CH3
Q.20 What is the effect on dipole moment of 1,2 dichloroethane when the temperature is increased?

2
Q.21 Most stable conformer of | (succinic acid)
2
(a) at very low pH (b) at very high pH.
Q.22 Draw more stable conformation for the following

(a)CH3 2
CH3 (b) CH3 CH3
| | |
CH3 CH3 CH3

(c)

CH3 H
CH CH
(d) (e) 3
CH 3 CH 3
H CH3
Q.22 Compare Rotational barrier.

(a) 3 2 2 3 3 2 3 3 3
(i) (ii) (iii)

(b) 2 2 2 2

(i) (ii)
CH 2
CH 2

(iii)
(c) Cl Cl Br Br I I F F
2 2 2 2 2 2 2 2

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

(d)

(i) (ii) (iii)

(e)

(i) (ii)

13
DPP NO- 5 Time: 15 minutes
Q.1 For the conformation of lowest energy estimate the atomic angles in the cation and the neutral
molecule drawn below. Provide one number only for each question.

:
O:
+

(A) C O
(B) C O C bond
(C) C O C
(D) C O C
Q.2 Which of the following is the most stable conformation of bromocyclohexane?
Br

(I) H (II) (III) (IV)

Br H
Br
H H Br
Br
(V)
H
(A) I (B) II (C) III (D) IV (E) V
Q.3 Which of the following correctly lists the conformations of cyclohaxane in order of increasing
energy?
(A) chair < boat < twist-boat < half-chair (B) half-chair < boat < twist-boat < chair
(C) half-chair < twist-boat < boat < chair (D) chair < twist-boat <boat < half-chair

Q.4
(A) on the same carbon (B) on adjacent carbons
(C) on C-1 and C-3 (D) on C-1 and C-4
(E) none of the above

Q.5 The Keq for the interconversion for the two chair forms of methylcyclohexane at 25°C is 18. What %
of the chair conformers feature an axial methyl group?
(A) 95 (B) 75 (C) 50 (D) 25 (E) 5

Q.6 Which of the following describes the most stable conformation of trans-1-tert-butyl-3-
methylcyclohexane
(A) Both groups are equatorial
(B) Both groups are axial
(C) The tert-butyl group is equitorial and the methyl group is axial
(D) The tert-butyl group is axial and the methyl group is equitorial
(E) None of the above

Q.7 Name the compound shown below.

Cl Cl

(A) trans-1, 2-dichlorocyclohexane (B) cis-1, 2-dichlorocyclohexane

(C) trans-1, 3-dichlorocyclohexane (D) cis-1, 3-dichlorocyclohexane
(E) trans-1, 4-dichlorocyclohexane

14
Q.8 What can be said about the magnitude of the equilibrium constant K for the following process?
H H

CH(CH3)2 CH3
H H
CH3 CH(CH3)2
(A) K = 1 (B) K > 1
(C) K < 1 (D) No estimate of K can be made

Paragraph for Question Nos. 9 to 11

Groups bonded by only a sigma ( ) bond (i.e., by a single bond) can undergo rotation about that
bond with respect to each other. The temporary molecular shapes that result from rotation of groups
about single bonds are called conformations of a molecule. Each possible structure is called a
conformer. An analysis of the energy changes associated with a molecular undergoing rotation
about single bonds is called conformational analysis.

Q.9 Most stable conformer of given compound is

2 2
F F OH
HH H
H H H OH H H H
(A) (B) (C) (D)
H H HO
H H H F F
OH H H
Q.10 Most Stable conformer of

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

Q.11 Which of the following pairs of structures represent conformational isomers?

CH3 CH3
H H H CH3
(A) (B)
H H H H
CH3 H

H
H
Br H H H H
(C) (D) H
Cl Br
Cl H H
H
H H

15
Q.12 Which of the following pairs of structures represent conformational isomers?

(A) and (B) and

(C) and (D) C and C

Q.13 Draw the Newmann projection formula of the most stable conformation of 3-hydroxy propanal
across C2 and C3.

Q.14 (a) Below are six conformations for a specific compound. With respect to the biggest groups,
determine which structure are eclipsed, anti, gauche, highest in energy and lowest in energy.
Me Me Me
H H Et
H H
(Pr = propyl)
H
Pr Me Pr Me Pr Me
Et
Et H
(A) (B) (C)

H Me H
Me Et Me
Et
Et H
Pr Me Pr Me Pr Me
H H
H
(D) (E) (F)

+1 +1 +1 +1 +1

Anti All Gauche All eclipsed Highest in Lowest in

energy energy

Q.15 The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at 25°C. Calculate the
percentage of the axial conformer at the temperature.

Q.16 Following eclipsed form of propane is repeated after rotation of

CH3
H

H H
H H
(A) 45° (B) 90° (C) 120° (D) 180°

16
DPP NO- 6 Time: 15 minutes

Q.1 Column I ColumnII

CH3
(A) H (P) cis-form
CH3
CH3
(B) (Q) trans-form
CH3
CH3
(C) (R) Keq is greater than one or equal to one when compound
CH3
undergo flip.
CH3

(D) (S) Keq is less than one when compound undergo flip.
CH3

Q.2 Write correct order of stability of different form of following compound X with suitable reason.
Me

CMe3
Me Me
Me
(I) (II) (III) (IV)
Me3C
CMe3 CMe3
Me

Me3C

Et
CH3
Q.3 Identify most stable form of given compound

CH3 Et Et
Et
(A) (B) (C) (D)
Et CH3 CH3
CH3

Q.4 Dipole moment of a compound W CH2 CH2 W is 1.5 D. If dipole moment of its gauche form is
6.0 D. what will be mol fraction of its anti form.

17
Q.5 Compare stability:
OH
OH HO
(a) HO and

OH

(b) HO and
OH
HO

(c) and

(d) and

(e) and

(f) and

(g) and

(h) and

Q.6 Draw 1,2,3,4,5,6-hexamethyle cyclohexane in which all

(a) methyl at axial position (b) methyl at equitorial position.

Q.7 Draw most stable form of methyl-cyclohexane.

18
Q.8 Compare stability of the following:

(a) (b)

(c) (d)

Q.9 Draw structure & compare stabilities of following

(a) cis & trans 1, 2 dimethyl cyclohexane.
(b) cis & trans 1, 3 dimethyl cycohexane.

Q.10 Explain:
R
H
Keq

R Keq
H 1
CH3 18
CH2 CH3 23
CH3
CH 38
CH3
3800

19