1.

The least stable conformation of butane is:

H H
3
C
H
H
H
H
3
C
H H
CH
3
H
CH
3 H
CH
3
H
H
H
H
H
3
C
CH
3
H
H
H
CH
3
H
H
CH
3
H
H
CH
3
I II III
IV V
H
A) I B) II C) III D) IV
E) V

2. The preferred conformation of cis -3-tert-butyl-1-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the molecule exists in a boat conformation.


3. What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?
H
H
3
C
H
CH
3
CH
3
H
H
H
3
C
H
CH
3
H
H
3
C
CH
3
H
CH
3
H
I II III
H
CH
3
H
H
3
C
V IV


A) I B) II C) III
D) IV
E) V
4. The most stable conformation of butane is:
H H
3
C
H
H
H
H
3
C
H H
CH
3
H
CH
3 H
CH
3
H
H
H
H
H
3
C
CH
3
H
H
H
CH
3
H
H
CH
3
H
H
CH
3
I II III
IV V
H


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

5. The most stable conformation of 1,2-dibromoethane is:
H
Br H
H
Br
H
H Br
H
H
H
Br H H
Br
H
Br
H Br H
H
H
H
Br
Br H
H
H
Br
H
I II III
IV V
A) I B) II C) III D) IV E) V


6.

The most stable conformation of 2,3-dibromobutane, viewed through the C-2C-3 bond :
H
Br H
3
C
H
Br
H
3
C
H Br
CH
3
CH
3
H
Br H H
3
C
Br
CH
3
Br
H Br H
3
C
H
H
CH
3
Br
H H
3
C
Br
Br
H
H
3
C
I II III IV V


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

7. The most stable conformation of 3-br omo-2-methylpentane, viewed through the
C-3C-4 bond (i.e., C-3 in the front, C-4 in the back):
Br H
CH(CH
3
)
2
H
CH
3
H
III
H
CH(CH
3
)
2
H
Br
CH
3 H
II
H Br
CH(CH
3
)
2
CH
3
H
H
I
CH(CH
3
)
2
Br
H
H
CH
3
H
IV
CH
3
H
CH
3
CH
2
CH
3
H
Br
V

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

8 . In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are:
A) one axial, one equatorial.
B) both axial.
C) both equatorial.
D) alternating between being both axial and both equatorial.
E) None of the above


9. The most stable conformation of 3-br omo-2-methylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):

H
CH
2
CH
3
H
3
C
Br
CH
3 H
II
CH
3
H
CH
3
H
CH
3
Br
I
CH
3
H
CH
3
CH
2
CH
3
H
Br
V
Br H
CH(CH
3
)
2
H
CH
3
H
III
CH
2
CH
3
Br
H
CH
3
CH
3
H
IV


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

10. The most stable conformation of 2,3-dimethylpentane, viewed through the
C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):
H
H H
3
C
CH
3
CH
2
CH
3 H
II
CH
3
H
CH
3
CH
3
CH
2
CH
3
H
I
CH
3
H
CH
3
CH(CH
3
)
2
H
H
3
C
V
CH
3
H
CH(CH
3
)
2
CH
3
H
H
III
CH
3
H
CH
3
CH
3
H
H
3
CH
2
C
IV

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

11. The most stable conformation of cis-1-tert-butyl-2-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the twist boat conformation is adopted.

12. The most stable conformation of trans-1-tert-butyl-2-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the molecule is in the half chair conformation.

13. The most stable conformation of trans-1-tert-butyl-3-methylcyclohexane is the one in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the twist boat conformation is adopted.

14. In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are:
A) one axial, one equatorial.
B) both axial.
C) both equatorial.
D) alternating between being both axial and both equatorial.
E) None of the above

15. The most stable conformation for 1,2-ethanediol (ethylene glycol) is shown below. It is
the most stable conformation because:

OH H
H
H
OH
H

A) this corresponds to an anti conformation.
B) in general, gauche conformations possess the minimum energy.
C) it is stabilized by intramolecular hydrogen bonding.
D) it is a staggered conformation.
E) it has the highest energy of all the possibilities.
16. The graph below is a plot of the relative energies of the various conformations of:
0
o
60
o
120
o
180
o
240
o
300
o
360
o
R
e
l
a
t
i
v
e

e
n
e
r
g
y
Angle of rotation
A) Ethane
B) Propane
C) Chloroethane
D) 1-Chloropropane (C1-C2 rotation)
E) Butane (C1-C2 rotation)



17. The graph below is a plot of the relative energies of the various conformations of:
0
o
60
o
120
o
180
o
240
o
300
o
360
o
R
e
l
a
t
i
v
e

e
n
e
r
g
y
Angle of rotation
A) 2-chloropropane B) 1,3-dichloropropane
C) 2-methylpropane
D) Butane (C1-C2 rotation)
E) Butane (C2-C3 rotation)

18. Consider the graph below, which is a plot of the relative energies of the various
conformations of hexane, viewed through the C2-C3 bond. The conformations
corresponding to the 60
o
and 300
o
are:
0
o
60
o
120
o
180
o
240
o
300
o
360
o
R
e
l
a
t
i
v
e

e
n
e
r
g
y
Angle of rotation
A) Eclipsed B) Staggered, and gauche C) Staggered and anti
D) More stable than the conformation at 180
o

E) None of the above


19. Which conformation of trans-1-isopropyl-3-methylcyclohexane would be present in
greatest amount at equilibrium?
A) The conformation with the methyl group equatorial and the isopropyl group axial
B) The conformation with the methyl group axial and the isopropyl group equatorial
C) The conformation with both groups axial
D) The conformation with both groups equatorial
E) The twist boat conformation.



20. Consider the graph below, which is a plot of the relative energies of the various
conformations of 2,3-dimethylbutane, viewed through the C2-C3 bond. The
conformations corresponding to the 120
o
and 240
o
are:
0
o
60
o
120
o
180
o
240
o
300
o
360
o
R
e
l
a
t
i
v
e

e
n
e
r
g
y
Angle of rotation
A) Eclipsed, more stable than the conformation at 0
o

B) Eclipsed, more stable than the conformation at 180
o

C) Staggered, more stable than the conformation at 0
o

D) Staggered, less stable than the conformation at 180
o

E) Two of the above are true
21. Which conformation represents the most stable conformation of trans-1-bromo-4-
methylcyclohexane?
CH
3
Br
Br
CH
3
CH
3
Br
Br
H
3
C
Br
CH
3
I II III
IV V

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

22. Which of the following can be described as cis isomers?

CH
3
CH
2
CH
3
Cl
CH
3
Br
HO
CH
3
HO
Br
F
I II III IV V


A) I
B) II, V C) III, IV
D) I, III and IV
E) None of the above are cis isomers.

23. The least stable conformation of cyclohexane is the:
A) boat.
B) twist boat. C) chair. D) half-chair.
E) twist chair.

24. Which of the following can be described as trans isomers?

CH
3
CH
2
CH
3
Cl
CH
3
Br
HO
CH
3
HO
Br
F
I II III IV V

E) None are trans isomers.
25. Which of the following will have the same energy after undergoing ring flip?

CH
2
CH
3
CH
2
CH
3
Cl
CH
3
OH
HO
CH
3
HO
Br
F
I II III IV V



A) I
B) II, V C) III, IV
D) I, III and IV
A) I B) II C) III D) IV E) V
26. The twist boat conformation is the preferred conformation for this compound.
A) cis-1,4-Di-tert-butylcyclohexane
B) trans-1,4-Di-tert-butylcyclohexane
C) cis-1,3-Di-tert-butylcyclohexane
D) trans-1,2-Di-tert-butylcyclohexane



27. The structures
CH
3
H
CH
3
H
CH
3
H CH
3
H

represent:
A) a single compound.
B) Geometricalisomers. C) meso forms.
D) diastereomers.
E) conformational isomers.

28. cis-1,3-Dibromocyclohexane is represented by structure(s):

Br
H H
Br
Br
H
H
Br
H
Br
H
Br
I II III
A) I B) II C) III D) II and III
E) I and II

1: B 2: D 3: B
4: C 5: C 6: C 7: A
8: A
9: E 10: D
11: B 12: D 13: B 14: A 15: C
16:D
17: E 18: B 19: B 20: A
21: A
22: B
23: D
24: C
25: E 26: A
27: A 28: A

30. Draw the bond-line structural formula corresponding to the most stable conformation of
the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane
30:
Br


31. Draw the Newman projection formula for the gauche conformation of the C2-C3 bond
in pentane.
31:
H H
CH
3
H
CH
2
CH
3 H

32. Draw the Newman projection formula for the most stable conformation of the C2-C3
bond in 3-methylpentane.
32:
H H
CH
3
CH
2
CH
3
CH
3 H


29. What is the relationship between alcohols I and II?
H
CH
3
OH
H
H
CH
3
H
OH
I II

A) different conformations of the same compound. B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
29: D