MULTIPLE CHOICE QUESTIONS

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

1. What is the correct IUPAC name for the following compound?

O
A) 2-Methyl-5-heptanone
B) 7-Methyl-4-octanone
C) 6-Isopropyl-4-octanone
D) Isobutyl propyl ketone
E) 1,1-Dimethyl-4-heptanone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

2. What is the correct structure for 7-methyl-4-octanone?

O

O O III
I II O

IV V

A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

3. What is the correct IUPAC name for the following compound?

O
A) 5,5-Dimethyl-2-heptanone
B) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
C) 5-Ethyl-5-methyl- 2-hexanone
D) 5,5-Dimethyl-2-octanone
E) 3,3-Dimethyl-6-heptanone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

4. What is the correct structure for 5,5-dimethyl-2-heptanone?

O

O O
I O II III

O
IV V

A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

5. A correct name for the following compound would be which of those below?

O
H

A) 2,5-Dimethyl-6-hexanal
B) 2,5-Dimethylhexanal
C) 2-Aldehydoisohexane
D) 3,5-Dimethylheptanone
E) 1-Hydro-2,5-dimethyl-1-hexanone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy

6. What is the correct structure for 2,5-dimethylhexanal?

O O

H
I
II O III

O O

H H

IV
V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

7. What is the correct IUPAC name for the following compound?

O

A) 5,5-Dimethyl-2-heptanone
B) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
C) 5,5-Dimethylcycloheptanone
D) 4,4-Dimethylcycloheptanone
E) 3,3-Dimethylcycloheptanone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

8. What is the correct IUPAC name for the following compound?

O

A) 2,4-dimethyl-2-pentenone
B) 2,5-dimethylcyclopenten-3-one
C) 2,4-dimethylcyclopent-2-enone
D) 3,5-dimethylcyclopent-2-enone
E) 2-methyl-5-methylcyclopent-2-enone
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

9. What is the correct IUPAC name for the following compound?

O
A) 1,1,2-Trimethyl-1,3-hexenone
B) 1,2-Dimethyl-1,3-hexenone
C) 2,3-Dimethyl-1,3-heptenone
D) 2,3-Dimethyl-2-hepten-4-one
E) 5,6-Dimethyl-5-hepten-4-one
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

10. What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

O

O O
I II
III

IV O
V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

11. O

A correct name for C6H5CH2CH2CH is?

A) 3-Benzylpropanone
B) 3-Phenylpropanal
C) 3-Benzylpropanal
D) Nonanone
E) Nonanal
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

12. What is the correct structure for 3-phenylpropanal?

O O

II III
I
O

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

13. What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

O Ph O OH O

Ph OH OH III Ph
II
I
Ph OH OH O

IV O V Ph

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

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

14. Which is the proper name for the structure shown?

CHO

Cl
CH3
A) 2-Chloro-5-aldehydotoluene
B) 6-Chloro-3-aldehydotoluene
C) 2-Methyl-4-aldehydochlorobenzene
D) 4-Chloro-3-methylbenzaldehyde
E) 4-Methyl-5-chloro-2-benzaldehyde
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

15. What is the correct structure for 4-chloro-3-methylbenzaldehyde?

O
O O

H
H H

Cl

I II
Cl III
Cl
O
H

H
O
Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

16. What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

O NO2
O

O2N NO2
I II

NO2 O
NO2
O
O2N
O2N H
H

NO2

III IV

O2N H

O
NO2

V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

17. What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

O
O

Cl
I Cl
II

O
O

H
H

Cl

IV
Cl III

Cl O

V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

18. What is the correct structure for 7-bromo-1-octyn-4-one?

Br
Br Br

O
O O
I II III

Br

Br

O
IV V O
A) I
B) II
C) III
D) IV
E) V
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

19. What is the correct IUPAC name for the following compound?
Br
O

A) 2-Methyl-2-bromobutanone
B) (S)-2-Bromo-2-methylcyclobutanone
C) (R)-2-Bromo-2-methylcyclobutanone
D) (S)-1-Bromo-1-methyl-2-cyclobutanone
E) (R)-1-Bromo-1-methyl-2-cyclobutanone
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

20. What is the correct IUPAC name for the following compound?
O

Cl H
A) (S)-3-chloro-1-hexanone
B) (S)-1-chloro-3-hexanone
C) (R)-3-chlorocyclohexanone
D) (S)-3-chlorocyclohexanone
E) (S)-1-chloro-3-cyclohexanone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

21. O

CH3 CH CH2 C CH CH3

What is the IUPAC name for OH C 6H 5 ?

A) 4-Oxo-5-phenyl-2-hexanol
B) 5-Hydroxy-2-phenyl-3-hexanone
C) 2-Hydroxy-5-phenyl-4-hexanone
D) 2-Hydroxypropyl-1-phenylethyl ketone
E) 5-Hydroxy-3-keto-2-phenylhexane
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

22. Which is the proper name for the structure shown?

O2N
O
NO2

A) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
B) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
C) 3-Methyl-5-(2,5-dinitrophenyl)pentanal
D) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
E) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

23. Which is the proper name for the structure shown?

O
Cl

A) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
B) 3-Methyl-5-(4-chlorophenyl)hexanol
C) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
D) 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
E) 3-Methyl-5-(4-chlorophenyl)hexanal
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

24. Which is the proper name for the structure shown below?

Br
O

A) 7-Bromo-1,4-octynal
B) 7-Bromo-1,4-octynone
C) 2-Bromo-5,7-octynal
D) 7-Bromo-7-methyl-1-heptyne-3-ketone
E) 7-Bromo-1-octyn-4-one
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

25. What is the correct structure for (R)-7-bromo-1-octyn-4-one?

Br
Br

Br
O
O O
I II III

Br

Br

O
IV V O
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

26. What is the correct structure for (S)-7-bromo-1-octyn-4-one?

Br
Br

Br
O
O O
I II III

Br

Br

O
IV V O
A) I
B) II
C) III
D) IV
E) V
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

27. Which is the IUPAC name for the structure shown below?
Br H

O
A) (R)-5-Bromo-2-heptanal
B) (S)-5-Bromo-2-heptanal
C) (R)-5-Bromo-2-heptanone
D) (S)-5-Bromo-2-heptanone
E) (R)-3-Bromopentyl methyl ketone
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

28. Which is the IUPAC name for the structure shown below?
H Br

O
A) (R)-5-Bromo-2-heptanal
B) (S)-5-Bromo-2-heptanal
C) (R)-5-Bromo-2-heptanone
D) (S)-5-Bromo-2-heptanone
E) (R)-3-Bromopentyl methyl ketone
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

29. What is the correct structure for (R)-5-bromo-2-heptanone?

O
Br H Br H
Br H
H

O O
I II III

H Br
H

H Br O O
V
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

30. What is the correct structure for (S)-5-bromo-2-heptanone?

O
Br H Br H
Br H
H

O O
I II III

H Br
H

H Br O O
V
IV
A) I
B) II
C) III
D) IV
E) V
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

31. Which is the IUPAC name for the structure shown below?

O
A) 5-Cyclohexyl-2-hexanal
B) 5-Cyclohexyl-2-hexanone
C) 5-Cyclohexyl-5-methyl-2-pentanone
D) 5-(1-Methylcyclohexyl)-2-pentanone
E) 4-(1-Methylcyclohexyl)-2-butanone
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

32. What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

O O III O
I II

O
O V
IV
A) I
B) II
C) III
D) IV
E) V
Ans:

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

33. What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

O O III O
I II

O
O V
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

34. What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

O O III O
I II

O V O
IV
A) I
B) II
C) III
D) IV
E) V
Ans:

Topic: Physical Properties, Relationships, Stereochemistry

Section: 16.3
Difficulty Level: Easy

35. Which of the compounds listed below would you expect to have the highest boiling
point? (They all have approximately the same molecular weight.)
A) Pentane
B) 1-Butanol
C) Butanal
D) 1-Fluorobutane
E) Diethylether
Ans:
Topic: Reagents
Section: 16.4
Difficulty Level: Easy

36. LiAlH4 (LAH) cannot be used to convert carboxylic acids to the corresponding
aldehydes because:
A) LAH is not sufficiently reactive.
B) RCOOH is converted into RCOOLi.
C) RCOOH is reduced to RCH2OH.
D) RCOOH is reduced to RCH3.
E) RCOOH is converted into R2C=O.
Ans:

Topic: Reagents
Section: 16.4
Difficulty Level: Easy

37. Identify the reagent(s) that would bring about the following reaction:

CH3CH2CH2COCl CH3CH2CH2CHO
A) H2/Ni
B) Li/liq.NH3
C) LiAlH[OC(CH3)3]3, ether
D) NaBH4, CH3OH
E) LiAlH4, ether
Ans:
Topic: Reaction Products
Section: 16.4 and previous chapters
Difficulty Level: Medium

38. Select the structure of the major product in the following reaction.
i) BH3
?
ii) H2O2,OH-, H2O

A) Ethylbenzene
B) 1-Phenylethanol
C) Acetophenone
D) 2-Phenylethanal
E) Vinylbenzene
Ans:
Topic: Reaction Products
Section: 16.4 and previous chapters
Difficulty Level: Medium

39. Select the structure of the major product in the following reaction.
i) BH3
?
ii) H2O2,OH-, H2O
OH O
OH

I II III

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium

40. What is the final product, Z, of the following synthesis?

1. LiAlH(O-t-Bu)3
1. KMnO4, OH-, heat SOCl2 ether, -78 oC
CH3 X Y Z
2. H3O+ 2. H2O

O O O O O
COAl(t-Bu)2 COCH3 CH COLi COH

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

41. Which of the following procedures would not yield 3-pentanone as a major product?
A) CH3CH2MgBr H3O+
CH3CH2CN
ether
B) 1. O3

2. Zn/H+

C) CH3CH2Li H3O+
CH3CH2CN
ether
D) H
CH3CH2MgBr H3O+ PCC

ether CH2Cl2
O
E) CH3CH2MgBr H3 O+
CH3CH2CO2H
ether
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

42. A good synthesis of

H
O

would be:
H H

H2O, H2SO4
I
H2O, H2SO4
I HgSO 4
HgSO4
H
1. Sia2BH
II
2. H2O2, NaOH
H CN 1. DIBAL-H/-78oC
II 1. O3 2. H2O
III
2. Zn, HOAc
H
OH 1. KMnO4, NaOH, heat
IV
1.+O3
2. H3O
III
2. Zn/H+

OH
1. KMnO4, NaOH, heat

IV 2. H3O+

A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

43. A good synthesis of

H
O

would be:
H H

H2O, H2SO4
I
H2O, H2SO4
HgSO
I 4
H HgSO4
1. Sia2BH
II
2. H2O2, NaOH
H 1. DIBAL-H/-78oC
COOCH3
II
1. O3
III 2. H2O
2. Zn, HOAc

OH H
1. KMnO4, NaOH, heat
IV
2. H3O+
1. O3
III
2. Zn/H+

OH
1. KMnO4, NaOH, heat

IV 2. H3O+

A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

44. A good synthesis of

H
O

would be:
H H

H2O, H2SO4
I
H2O, H2SO4
HgSO
I 4
H HgSO4
1. Sia2BH
II H
2. H2O2, NaOH
H
1. O3
II 1. O3
III 2. Zn/H+
2. Zn, HOAc

OH 1. KMnO4, NaOH, heat

IV
2. H3O+
COCl 1. LiAl(OC(CH3)3)3H
III
2. H3O+

OH
1. KMnO4, NaOH, heat

IV 2. H3O+

A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

45. A good synthesis of

H
O

would be:
H H
H2O, H2SO4
I
HgSO4H2O, H2SO4
I
H HgSO4
1. Sia2BH
II
2. H2OH2, NaOH
H
1. O3 1. O3
IIIII
2. Zn, HOAc
2. Zn/H+

OH 1. KMnO4, NaOH, heat

IV
2. H3O+
PCC

III CH2Cl2
OH

OH
1. KMnO4, NaOH, heat

IV 2. H3O+

A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

46. A good synthesis of

H
O

would be:
H H
H2O, H2SO4
I
HgSO41. BH3
I
H
2.H2O2, NaOH
1. Sia2BH
II
2. H2O2, NaOH
H CN 1. DIBAL-H/-78oC
II 1. O3 2. H2O
III
2. Zn, HOAc

OH 1.COOCH
KMnO4,1.NaOH, heatoC
DIBAL-H/-78
IV 3
III 2. H3O+ 2. H2O

COCl 1. LiAl(OC(CH3)3)3H
IV
2. H3O+

A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium

47. Which synthesis or syntheses would yield propanal?

A) PCC
CH3CH2CH2OH
CH2Cl2
B) O
LiAlH[OC(CH3)3]3
CH3CH2CCl
ether, -78 oC
C) 1. Sia2BH
CH3C CH
2. H2O2, OH-
D) All of these
E) None of these
Ans:

Topic: Reaction Products

Section: 16.4
Difficulty Level: Hard

48. Select the structure of the major product in the following reaction.

i) H2, Lindlar catalyst

?
ii) O3
iii)Zn, CH3CO2H

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol
Ans:
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard

49. Select the structure of the major product in the following reaction.

i) H2, P-2
?
ii) O3
iii)Zn, CH3CO2H

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol
Ans:

Topic: Reaction Products

Section: 16.4
Difficulty Level: Hard

50. Select the structure of the major product in the following reaction.

i) H2, Ni2B
?
ii) O3
iii)Zn, CH3CO2H

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol
Ans:
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard

51. Select the structure of the major product in the following reaction.

i) Li, NH3(l)
?
ii) O3
iii)Zn, CH3CO2H

A) 3-Methylhexanal
B) 4-Methyl-1-hexanol
C) 4-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol
Ans:
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard

52. Select the structure of the major product in the following reaction.

i) H2, Lindlar catalyst

?
ii) O3
iii)Zn, CH3CO2H
O OH O

H H

III
I II

OH
O

OH
O

V
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Synthesis
Section: 16.4
Difficulty Level: Hard

53. A good synthesis of

H
O

would be:
H
H2O, H2SO4
I
HgSO4
H
1. Sia2BH
II
2. H2O2, NaOH
H
1. O3
III
2. Zn, HOAc

OH 1. KMnO4, NaOH, heat

IV
2. H3O+
A) I
B) II
C) III
D) IV
E) All of these are equally useful.
Ans:
Topic: Reaction Products
Section: 16.5 and previous chapters
Difficulty Level: Medium

54. Select the structure of the major product in the following reaction.
H2SO4
?
HgSO4, H2O

A) Ethylbenzene
B) 1-Phenylethanol
C) Acetophenone
D) 2-Phenylethanal
E) Vinylbenzene
Ans:

Topic: Reaction Products

Section: 16.5 and previous chapters
Difficulty Level: Medium

55. Select the structure of the major product in the following reaction.
H2SO4
?
HgSO4, H2O
OH O

I II III

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

Topic: Reaction Products

Section: 16.5
Difficulty Level: Medium
 56. Select the structure of the major product in the following reaction.
i.) KMnO4, OH-, hot
?
ii) H3O+

OH OH

I II III

OH O

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

Topic: Reaction Products

Section: 16.5
Difficulty Level: Medium

57. Select the structure of the major product in the following reaction.
i.) KMnO4, OH-, hot
?
ii) H3O+
A) cyclopentanol
B) 1-cyclopentylcyclopentane
C) cyclopentanone
D) cyclopentene
E) 1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane
Ans:
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium

58. Which of the reactions listed below would serve as a synthesis of acetophenone,
O

C6H5CCH3 ?
A) OH

PCC

CH2Cl2

AlCl3
B) C6H6 + CH3COCl
C) ether H 3O +
C6H5CN + CH3Li
D) Answers A) and B) only
E) Answers A), B), and C)
Ans:

Topic: Synthesis
Section: 16.5
Difficulty Level: Medium

59. Which of the following would yield 3-pentanone as the major product?
A) ether H3O+
CH3CH2CN + CH3CH2Li Product
B) ether H O+
3
CN + MgBr Product
C) PCC

CH2Cl2
OH
D) Two of these
E) All of these
Ans:
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium

60. Which of the following is not a synthesis of benzophenone,

C6H5CC6H5 ?
A) O
AlCl3
C6H6 + C6H5CCl
B) H2CrO4
(C6H5)2CHOH
acetone
C) 1. O3
(C6H5)2CH=CH2
2. Zn, HOAc
D) PCC
Ph2CHOH
CH2Cl2
E) All of the above will give benzophenone.
Ans:

Topic: Synthesis
Section: 16.5
Difficulty Level: Hard

61. Which of the following is a synthesis of 3-heptanone?

A) PCC 1. CH3CH2MgBr H2Cr2O4
CH3CH2CH2CH2CH2OH
CH2Cl2 2. H3O+ acetone
B) CH3(CH2)2CH2Li H3 O+
CH3CH2CN
ether
C) PBr3 NaCN CH3CH2MgBr H3O+
CH3CH2CH2CH2OH
ether ether
D) 1. O3

2. Zn/H+

E) All of the above are syntheses of 3-heptanone.

Ans: