Name: __________________________

1. Which one is bicyclo[3.3.1]nonane?

II

III

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

2. Which molecule is a meso compound?

H Cl Br Cl Br H H H Br Cl Br Cl Cl Cl Br H Br Br

A) B) C) D) E)

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

III

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3. I and II are:
OH HO NH2 NH2 II

I A) constitutional isomers. B) enantiomers. C) identical. D) diastereomers. E) not isomeric.

4. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) B) C) D) E)

2 3 4 5 6

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

HO Br Cl CH3 F Br

I
CH3 HO

II
CH3

III

CH2CH3

A) B) C) D) E)

IV V I II, V III, IV I, III and IV None of the above are trans isomers.

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6. Which structure(s) represent(s) diastereomer(s) of I?

H HO HO CH3 OH H H CH3 H HO H CH3 OH H OH CH3 H H H CH3 OH OH OH CH3 HO HO H CH3 H H OH CH3 H H HO CH3 OH OH H CH3

A) B) C) D) E)

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

II

III

IV

7. Draw a dash-wedge structure for (R)-5-methylhept-2-yne

8. A correct name for the following compound is:

Br

A) B) C) D) E)

4-bromo-3,8-dimethylbicyclo[5.2.2]nonane 3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane 4-bromo-3,8-dimethylbicyclo[5.2.1]decane 7-bromo-2,6-dimethylbicyclo[5.2.0]nonane 4-bromo-3,8-dimethylbicyclo[5.2.0]nonane

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

H H3C OH CH2CH3 H CH3 OH CH2CH3 HO H CH3 CH2CH3 HO CH3 H CH2CH3 H CH2CH3 OH CH3

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

III

IV

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10. The molecules below are:

H H H H

CH3 Cl

Cl CH3

A) B) C) D) E)

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

11. The least 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):
CH3 H H CH3 CH3 CH2CH3 H H3C CH3 H CH2CH3 H H H3C CH3 H CH2CH3 CH3

I
H H H3C H3C CH2CH3 CH3

II
CH3 H3C H H

III

CH3 CH(CH3)2

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

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12. trans-1,2-Dibromocyclohexane is represented by structure(s):

Br Br H H Br H H Br Br H Br H

A) B) C) D) E)

I I II III II and III I and II

II

III

13. Pairs of enantiomers are:

CH3 H3C Cl CH2CH2CH3 Cl CH3 CH3 CH2CH2CH3 H3C H Cl CH2CH2CH3

I
CH2CH2CH3 H3C H Cl

II
CH2Cl H H CH2CH2CH3

III

A) B) C) D) E)

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

14. I and II are:

OH

OH

Cl

Cl

A) B) C) D) E)

I constitutional isomers. enantiomers. identical. diastereomers. not isomeric.

II

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15. Which molecule has a plane of symmetry?

F Cl H Cl H H Cl H H CH3 H H CH3 CH3

A) B) C) D) E)

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

III

16. Consider the graph below, which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane, viewed through the C-2C-3 bond. The conformations corresponding to the 120o and 240o are:
Relative energy
0o 60o 120o 180o 240o 300o 360o

A) B) C) D) E)

Angle of rotation Eclipsed, more stable than the conformation at 0o Eclipsed, more stable than the conformation at 180o Staggered, more stable than the conformation at 0o Staggered, less stable than the conformation at 180o Two of the above are true

17. How many moles of hydrogen (H2) will react with (trans, trans)-hepta-3,5-dien-1-yne? A) 1 B) 2 C) 3 D) 4 E) 5
2

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18. CH3CHBrCHBrCHClCH3 is the generalized representation of what number of stereoisomers? A) 4 B) 5 C) 6 D) 7 E) 8

19. A correct IUPAC name for the following compound is:

OH

Cl

A) B) C) D) E)

4-propyl-5-chloro-3-heptanol 4-propyl-3-chloro-5-heptanol 4-(1-chloropropyl)-3-heptanol 5-chloro-4-propyl-3-heptanol 3-hydroxy-4-propyl-5-chloroheptane

20. 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

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