ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN.

DPP-1

1. Which of the following is the staggered conformation for rotation about the C1–C2 bond in the following
structure ?

(I) (II) (III)

(IV) (V)

(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. and are

(A) Chain isomers (B) Metamers (C) Positional isomers (D) Conformers

4. 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)

5. Comprehensive :
Torsional and steric strain Energy :
Type of inter action Energy increases
H, H Eclipsing 1 kcal/mole
H, CH3 Eclipsing 1.5 kcal/mole

M S Chouhan -Author- Kota M S Chouhan

[1]
 CH3, CH3 Eclipsing 4 kcal/mole
CH3, CH3 Gauche 0.9 kcal/mole

(i) Based on above data calculate the energy difference between the two conformes given below.

(A) 1.8 kcal/mole (B) 0.9 kcal/mole (C) 2.7 kcal/mole (D) 3.6 kcal/mole

(ii) Calculate the rotational barrier to designate bond.

(A) 4 kcal/mole (B) 4.5 kcal/mole (C) 5 kcal/mole (D) 5.5 kcal/mole

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

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

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M S Chouhan -Author- Kota M S Chouhan

[2]
8. (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.

(Pr = propyl)

Anti

For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-2
1. Most Stable conformer of

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

2. Most stable conformer of given compoun d is

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

3. Name the compound shown below.

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

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

4. Which of following equilibrum is not rapid at room temperature ?

3

(A) (B)

(C) (D)

5. Cyclohexane-1,4-dione is a polar compound, having dipole moment value of 1.2 D. If mol fraction of its chair
form is 0.80, what will be the dipole moment of twisted boat form?
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M S Chouhan -Author- Kota M S Chouhan

[1]
6. 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.
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For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-3

1. 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

2. 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
3. Which of the following is the most stable conformation of bromocyclohexane ?

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

(V)

(A) I (B) II (C) III (D) IV (E) V

4. 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

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

6. The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at 25ºC. Calculate the percentage of the
axial conformer at the temperature.
(A) 40% (B) 60% (C) 80% (D) 100%

7. 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 equatorial and the methyl group is axial
(D) The tert-butyl group is axial and the methyl group is equatorial
(E) None of the above

M S Chouhan -Author- Kota M S Chouhan

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

3 2
3

3 3 2

(A) K = 1 (B) K > 1

(C) K < 1 (D) No estimate of K can be made

9. Column I Column II

(A) (P) cis-form

(B) (Q) trans-form

(C) (R) Keq is greater than one or equal to one when

compound undergo flip.

(D) (S) Keq is less than one when compound

undergo flip.

10. (a) Write Newman projections for the gauche and anti conformations of 1,2-dichloroethane (ClCH2CH2Cl)

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(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.

“Follow your dreams; they will give meaning to every step that you take.”

M S Chouhan -Author- Kota M S Chouhan

[2]
 For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-4

Q. Count the total number of Chiral Center.

1. 2. 3.

4. 5. 6.

7. 8. 9.

10. 11. 12.

13. 3 14. 15. 3

16. 17.

M S Chouhan -Author- Kota M S Chouhan

[1]
 For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-5

1. 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)

2. For each of the following pharmaceutical compounds, identify all stereogenic (i.e. all asymmetric carbon
atoms) and label the configuration of each as being either (R) or (S).

3 2

3. Indicate whether each of the following structure has the R configuration or the S-configuration.

(a) (b) (c) (d)

(e) (f) (g) (h)

(i) (j) (k) (l)

M S Chouhan -Author- Kota M S Chouhan

[1]
 (m) (n) (o) (p)

4. Indicate whether each of the following structure has the R configuration or the S-configuration.

(a) (b) (c)

(d) (e) (f)

(g) (h) (i)

(j) (k) (l)

(m) (n) (o)

(p) (q) (r)

(s) (t) (u)

M S Chouhan -Author- Kota M S Chouhan

[2]
 For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

[3]
ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-6
1. Find relationship between given pairs

Identical Enantiomer Diastereomer Constitutional Other

isomer

(1)

(2)

(3)

(4)

(5) & 3
3 2 2
2 2 3

(6) and 3
3 2
2

|
(7) and

(8) 3 2 3 &
2 3

(9)
(a) (b)

M S Chouhan -Author- Kota M S Chouhan

[1]
(10)

(a) (b)

2. Find relationship between given pairs

Identical Enantiomer Diastereomer Constitutional Other
isomer

(1)

(a)

(b)

(2)

(a)

(b)

(3)

(a) (b)

(4)

(a) (b)

(5)

(a) (b)

(6)

(a) (b)

M S Chouhan -Author- Kota M S Chouhan

[2]
 Identical Enantiomer Diastereomer Constitutional Other
isomer

(7)

(a) (b)

(c)

(8)

(a) (b)

(9)

(10)

(11)
3 3 3

3 3

(12)

3 3

(13)

3
3

(14)
3
3

[3]
 For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-7

Q.1 Find relationship between given pairs

Identical Enantiomer Diastereomer Constitutional Other
isomer

(1)

(a) (b)

(2)

(a) (b)

(3)

(a) (b)

(4)

(a) (b)

(5)

(a) (b)

(6)

(7)

(a) (b)

[1]
 Identical Enantiomer Diastereomer Constitutional Other
isomer

(8)

(a) (b)

(9)

(a) (b)

(10)

Q.2 Find relationship between given pairs

Identical Enantiomer Diastereomer Constitutional Other
isomer

(1)
(a) (b)

(2)

(a) (b) (c)

(3)

(a) (b)

(4)

(a) (b)

(5)

(a) (b)

(6)

(a) (b)

[2]
 Identical Enantiomer Diastereomer Constitutional Other
isomer

(7)

(a) (b)

(8)

(a) (b)

(9)

(a) (b)

(10)

(a) (b)

For Batter Understanding Watch This Animation Of Conformer

“There is always something nobody else can do except you......

everybody is unique in his own way so never feel inferior.”

M S Chouhan -Author- Kota M S Chouhan

[3]
ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-8

1. Which of the following depict the same stereoisomer?

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

2. Which of following pair represent diastereomers.

(A) (B)

(C) (D)

3. Which of following pair represent diastereomers.

(A)

(B)

(C)

(D)

M S Chouhan -Author- Kota M S Chouhan

[1]
4. Which pairs of the salts should have identical solubilities in methanol?

(I) (II)

(III) (IV)

(A) I & IV (B) I & III (C) I & II (D) II & IV

5. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, conformational isomers and different compounds that are not isomeric).

(A) _______________

(B) _______________

(C) _______________

(D) _______________

(E) _______________

M S Chouhan -Author- Kota M S Chouhan

[2]
 For Batter Understanding Watch This Animation Of Conformer

M S Chouhan -Author- Kota M S Chouhan