Chapter 5

MULTIPLE CHOICE QUESTIONS Stereochemistry

Answers on page 10
Topic: Identifications and Comparisons
1. Which of the following is the enantiomer of the following substance?
H

H
H
Br

A)
B)
C)
D)
E)

CH3

Br
H

CH3

CH3

CH3

Br
H

H
Br

I
II
I
II
III
It does not have a non-superposable enantiomer.
Both II and III

III

2. Which of the following molecules is achiral?

CO2H
H

H 3C
C C

HO2C
CH3

H
Cl

II

III

3. Hexane and 3-methylpentane are examples of:

A) enantiomers.
B) stereoisomers.
C) diastereomers.
D) constitutional isomers.
E) None of these
4. I and II are:
H3C

Cl
H

A)
B)
C)
D)
E)

CH2Cl
H

H
CH2CH3

I
II
constitutional isomers.
enantiomers.
non-superposable mirror images.
diastereomers.
not isomeric.

OH

HO

I
II
III
IV
V

CH2CH3

Br

OH

A)
B)
C)
D)
E)

CO2H

OH

H
CO2H

IV

CH3
HO

Br
CH2CH3

Chapter 5

5. Pairs of enantiomers are:

CH3
H3C

CH3

Cl

Cl

CH3

H3C

CH2CH2CH3

CH2CH2CH3

CH2CH2CH3

II

III
CH2Cl

CH2CH2CH3
H3C

Cl

H
CH2CH2CH3

IV
I, II and III, IV
I, II
III, IV
IV, V
None of the structures

A)
B)
C)
D)
E)

Cl

6. Chiral molecules are represented by:

CH3
H3C

Cl

Cl

C2H5

CH3

H 3C

C2H5

II
I
I, II, III, IV and V
I, II, III and IV
I and II
III and IV
IV alone

A)
B)
C)
D)
E)

7. The molecules shown are:

H

OH

Br
CH3

A)
B)
C)
D)
E)

OH

Br

C2H5

CH3

H
CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

Cl

H 3C

Cl

CH2Cl
H

C2H5

C 2H 5

III

IV

Chapter 5
The

8. The molecules shown are:

Cl

H3CH2C

Cl

and

Cl

CH2CH3

Cl

CH2CH3

A)
B)
C)
D)
E)

are

CH2CH3

enantiomers.
diastereomers.
constitutional isomers.
two conformations of the same molecule.
not isomeric.

9. The molecules shown are:

CH3

H
F

CH3
H

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

10. The molecules below are:

F

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
stereoisomers.

H
F
F

11. The molecules shown are:

CH3

Cl

Cl

CH3

Cl

Cl

CH3

A)
B)
C)
D)
E)

CH3

enantiomers.
diastereomers.
constitutional isomers.
two different conformations of the same molecule.
not isomeric.

Chapter 5

12. The molecules shown are:

H

CH3

OH

OH
H
H
CH3

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

13. The molecules shown are:

H
F

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

14. The molecules below are:

CH3

H
H

CH3

CH3
CH3

A)
B)
C)
D)
E)

structural isomers.
enantiomers.
diastereomers.
identical.
None of these

15. Cis-trans isomers are:

A) diastereomers.
B) enantiomers.
C) stereoisomers.
D) constitutional isomers.
E) More than one of these
Ans: E

Chapter 5

16. The molecules below are:

Cl

CH3
Cl

Br

A)
B)
C)
D)
E)

Br

CH3

II

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

17. The molecules below are:

CH3
H

CH3

H2N

CH3

H3C

A)
B)
C)
D)
E)

NH2

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

18. The molecules shown are:

A)
B)
C)
D)
E)

CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

19. The molecules below are:

Cl

CH3
F

Cl
H

A)
B)
C)
D)
E)

H
CH3

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

Chapter 5

20. The molecules below are:

H

H
H

Cl

CH3

CH3

Cl

A)
B)
C)
D)
E)

constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

21. Which molecule is achiral?

H

Cl

Cl

Br

Br

Cl

Br

Br

Cl

Cl

Br

Cl

Br

Br

I
II
I
II
III
More than one of these
None of these

A)
B)
C)
D)
E)

III

22. Which molecule is achiral?

H

Br

Br

Br

Cl

Cl

Br

Cl

Br

Br

Cl

Cl

A)
B)
C)
D)
E)

II
I
II
III
More than one of the above
None of the above

III

Chapter 5

23. The molecules below are:

H

A)
B)
C)
D)
E)

II
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these

24. The structures

H

CH3

CH3
CH3

H
CH3

represent:
A) a single compound.
B) enantiomers.
C) meso forms.
D) diastereomers.
E) conformational isomers.
25. Which pair of structures represents the same compound?
CH3
OH
H
H
OH
H
OH
CH3

CH3
H
OH
H
HO
OH
H
CH3

CH3
OH
H
H
HO
H
HO
CH3

CH3
H
HO
H
HO
H
OH
CH3

CH3
OH
H
OH
H
HO
H
CH3

II

III

IV

A)
B)
C)
D)
E)

I and II
II and III
III and IV
III and V
IV and V

Chapter 5

Topic: Specific names

26. (R)-2-Chlorobutane is represented by:
H3C

Cl

CH3

CH3
Cl

CH3

CH2Cl

CH2CH3

H3C

Cl

H3C

Cl

CH2CH3

CH2CH3

CH2CH3

CH2CH3

II

III

IV

CH3

CH2CH3

A)
B)
C)
D)
E)

I
II
III
IV
V

27. Which of the following represent (R)-2-butanol?

H

CH3

H
H3C

OH

OH

HO

CH3

HO

CH2CH3

CH2CH3

CH2CH3

CH3

II

III

IV

III and V
I, III, IV and V
I, IV and V
I and III
I, II, IV and V

28. Which structure represents (S)-1-chloro-1-fluoroethane?

H
CH3

CH3

A)
B)
C)
D)
E)

OH

CH2CH3

A)
B)
C)
D)
E)

Cl

Cl
CH3

II
I
II
III
More than one of the above
None of the above

Cl
F

III

Chapter 5

29. How many stereogenic centers are there in Lovastatin ( Mevacor : a cholesterollowering drug) ?
HO

O
O

(Lovastatin)
4
5
6
7
8

A)
B)
C)
D)
E)

Use the following to answer questions 30-31:

Consider the following compounds:
CH2OH
H

OH

CH3

HO

CH3

HO

CH3

HO

CH3

CH3
H

OH

H3C

CH3

OH

OH

II

III

IV

30. Which of the compounds above (I-IV) represent enantiomers?

A) I and II
B) II and III
C) III and IV
D) II and IV
E) III and IV
31. Which compound above (I-IV) is a meso compound?
A) I
B) II
C) III
D) IV
E) None of these

Chapter 5

Svar Extra Stereokemi

Frga
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

31

Svar
D
B
D
A
C
D
B
B
B
A
A
B
E
C
E
D
C
A
D
B
A
C
A
A
D
C
C
D
E
B
D

Rtt/Fel

10