ORGANIC CHEMISTRY

BYVINEET KHATRI SIR

EXCEL BATCH DPP. NO.52
1. 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 H
CH3 H CH3
H
(A) I (B) II (C) III (D) IV and V
2. 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

3. Which of the Newman projections shown below represents the most stable conformation about the C1–C2
bond of 1-iodo-2-methyl propane?

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

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

........................................................................................................................................................

........................................................................................................................................................

5. Draw the Newman structure for the most stable conformation of 1-bromopropane considering rotation about
the C1–C2 bond.

........................................................................................................................................................

........................................................................................................................................................
6. (a) Below are six conformations for a specific compound. With respect to the biggest groups, determine
which structures are eclipsed, anti, gauche, highest in energy and lowest in energy.

Me Me
H Me
H H Et H
(Pr = propyl)
H
Pr Me Pr Me Pr Me
Et Et H
(A) (B) (C)

Me
H Me Et Me
H Et

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

Anti All Gauche All eclipsed Highest in Lowest in

energy energy

7. In the boat conformation of cyclohexane, the “flagpole” hydrogens are located :

(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

8. Which of the following correctly lists the conformations of cyclohexane in order of increasing energy ?
(A) chair < boat < twist-boat < half-chair (B) half-chair < boat < twist-boat < chair
(C) chair < twist-boat < half-chair < boat (D) chair < twist-boat < boat < half-chair
(E) half-chair < twist-boat < boat < chair

9. Which conformer is at a local energy minimum on the potential energy diagram in the chair-chair interconversion
of cyclohexane ?
(A) half-chair (B) planar (C) boat (D) twist-boat
(E) fully eclipsed

10. Most stable conformer of given compoun d is

HO—CH 2—CH2—F
F F OH
H H OH H H H H
H H H
(A) (B) (C) (D)
H H H H H F OH
OH H H F

11. 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 mole fraction of its anti form.
......................................................................................................................................................

......................................................................................................................................................
 ORGANIC CHEMISTRY
BYVINEET KHATRI SIR
EXCEL BATCH DPP. NO.53

Q. Count the total number of Chiral Center.

CH 3
O CH
CH3 CH2 CH2 CH 2 CH2

1. CH CH2 2. 3. CH2 CH
CH CH C
CH3
O CH3 CH3 H
CH3

CH2 CH2
H 2C CH CH
O
CH2 CH2
4. H 2C CH OH 5. CH 6. NH2 – CH – COOH
CH2 CH2 CH |
CH2 CH2 CH3

CHO CHO CH3

H OH H OH H Me
7. 8. H OH 9.
H OH H OH H Et
CH2OH CH2OH C2H5

O
O
10. NH 11. 12. Ph – S – CH3

H
.. 16 O
+ As C2H5 ||
13. CH3 N Ph 14. 15. CH3 — S — Ph
D CH3 H ||
18 O

16. 17.
HO HO
Cholesterol Estrone
 ORGANIC CHEMISTRY
BYVINEET KHATRI SIR
EXCEL BATCH DPP. NO.54

S.No Compound Optically Chiral Achiral Optically No. of

active mole. mole. inactive Chiral Center

1.

2.

3.

4.

5.

Me

6.

Me

7.
S.No Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral Center

8.

9.

10. Hockey

11.

12.

13.

14.

15.
 ORGANIC CHEMISTRY
BYVINEET KHATRI SIR
EXCEL BATCH DPP. NO.55

1. Indiate whether each of the following structure has the R configuration or the s-configuration.

OH CH2–CH3 D
Cl
C CH3 C CH2 C Cl
(1) F H (2) CH –CH (3) CH3 (4) H
3 2
Br CHO H CH3

CH3 CMe NH2

Br Cl Br Cl
H Br
(5) (6) (7) (8) CH3 CH3 (9) C
H Br F OH
CD3
OH3

Br Cl I
I H OH
(10) F (11) (12) SH D
Cl Cl
F

2. Indicate the structure/s having R configuration.

CH2=Cl F CH2–OH
CH=CH2
C C C
(A) C (B) H C (C) HO (D) D
CH2–CH2–Cl CH3 OCH3
H CH3 3

OH NH2 T
COOH
3. The S-enantiomers of ibuprofen is reversible for its pain relieving properties. Which one of the structure
shown is S-ibuprofein?

( A ) (B)

(C) (D)
4. Compounds having even no of chiral center.

(A) (B)

Cl Cl

(C) (D)

Cl Cl

5. Count the total number of primary alcohol of C5H12O (excluding stereo).

6. Last digit of sum of total number of chiral center of compounds having R configuration only.

CH2–OH CH3 CH3 CH3 CH2–CH3

HO H Br H H Br CH3 H
(a) HO CH3 (b) H Cl (c) Br Br (d) H Br (e) Br CH3
CHCH2CH2–OH CH2–CH3 CH2–CH3 CH2–CH3 CH2–CH3

COOH
H OH
(f) H OH
COOH
 ORGANIC CHEMISTRY
BYVINEET KHATRI SIR
EXCEL BATCH DPP. NO.56

Determining the relationship between two non identical molecules

Two nonidentical molecules

Do they have the same molecular formula?

No Yes
not isomers isomers
Are the molecules named the same,
except for prefixes such as cis, trans, R, or S?

No Yes
constitutional stereoisomers
isomers
Are the molecules mirror
images of each other?

Yes No
enantiomers diastereomers

Read up the given FLOW CHART and identify the relationship between given pairs
1. Show how each pair of compounds is related

(1) HO OH and OH (2) and

OH

OH HO
(3) and (4) and

OH OH
CH3 Br
| | Me Me
C C H OH HO H
(5) Br and HOCH (6) and
H 2 H H OH H OH
CH2OH CH3
Me Me
CHO CH3
C C
(7) and (8) and HO
CH3 OH H
H CHO

H H
D
D D

(9) D and (10) and

H H H H
D
D

(11) and
2. Find relationship between given pairs

Identical Enantiomer Diastereomer Constitutional Other

isomer

OH OH OH

(1)
OH OH OH

(a) (b) (c)

(2)

CO2H CO2H

(a) (b)

H Me H H

(3)
Me H Me Me

(a) (b)

H H

(4)

(a) (b)

Cl Cl Cl
Cl

(5)

Br Br Br Br

(a) (b)

(6) OH OH
O O
(a) (b)
Me H Me H
O
(7) Me
H O
OH
O
(a) (b)
 Identical Enantiomer Diastereomer Constitutional Other
isomer

Cl Cl Cl Cl

(8)

H Me Me H

(a) (b)

Me H H
Br Br H
(9)
H
H H
(a) (b)

Cl
Cl
Cl Cl
(10)
Cl
Cl

(11)

(a) (b)
H Cl H
Et
(12) Cl H Cl
H
Cl Et
 ANSWER KEY
DPP-52
1. A 2. C 3. C

Et
Et Br
H H

4. 5.
H H
Me Me H H
Least stable CH3
conformer Most stable
conformer

E AC BFD B E
6.
Anti All Gauche All eclipsed Highest in Lowest in
energy energy

7. D 8. D 9. D 10. B
W W
H H H W
11.

H H H H
W H
(Anti) (Gauche)

a  0  g  6 .0 D T = 1.5 D

T = a xa + gxg xg  xa  1
1.5 = 6.0 × xg
xg = .25
x a  x g  1 .0

x a  1 – .25  .75

DPP-53
1. 1 2. 2 3. 3 4. 1 5. 4 6. 1 7. 2

8. 3 9. 0 10. 1 11. 3 12. 1 13. 1 14. 1

15. 1 16. 8 17. 4
 DPP-54

S.No Optically Chiral Achiral Optically No. of

active molecule molecule inactive Chiral Center

1. × ×   4

2.   × × 2

3. × ×   2

4.   × × 1

5.   × × 2

6. × ×   0

7.   × × 2

8.   × × 0

9. × ×   0

10.   × × 0

11.   × × 1

12.   × × 1

13.   × × 5

14. × ×   2

15. × ×   4

DPP-55
Q.1

1. S 2. R 3. R 4. R 5. 2R-3S 6. 2S-3S
7. 2S-3R 8. R 9. S 10. R 11. 1R-3R 12. 1S-2S

2. A 3. B 4. ABD 5. 4 6. 2
 DPP-56
Q.1.

1. Constitional 2. Enantiomers 3. Enatniomers 4. Chain isomers 5. Identical

6. Diastereomers 7. Diastereomers 8. Enantiomers 9. Conformers 10. Diastereomers

11. Identical

Q.2

Identical Enantiomer Diastereomer Constitutional isomer Other

1. (a, b) (a,c) (b,c)

2. 

3. 

4. 

5. 

6. 

7. 

8. 

9. 

10. 

11. 

12. 