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Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 16

Question type: Multiple Choice

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

O

a) 2-Methyl-5-heptanone c) 6-Isopropyl-4-octanone d) Isobutyl propyl ketone e) 1,1-Dimethyl-4-heptanone Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Easy

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

O

I

II

O O

V

a) I b) II c) III e) V Answer: D Topic: Nomenclature 1

III

Section: 16.2 Difficulty Level: Easy

3) What is the correct IUPAC name for the following compound? O

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 Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Easy

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

O

I

O

II

O

III

H

O

V

IV

a) I c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Easy

2

5) A correct name for the following compound would be which of those below? O H

a) 2,5-Dimethyl-6-hexanal c) 2-Aldehydoisohexane d) 3,5-Dimethylheptanone e) 1-Hydro-2,5-dimethyl-1-hexanone Answer: B 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 e) V Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Easy

7) What is the correct IUPAC name for the following compound? 3

O

a) 5,5-Dimethyl-2-heptanone b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone c) 5,5-Dimethylcycloheptanone e) 3,3-Dimethylcycloheptanone Answer: D 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 d) 3,5-dimethylcyclopent-2-enone e) 2-methyl-5-methylcyclopent-2-enone Answer: C Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

O

4

a) 1,1,2-Trimethyl-1,3-hexenone b) 1,2-Dimethyl-1,3-hexenone c) 2,3-Dimethyl-1,3-heptenone e) 5,6-Dimethyl-5-hepten-4-one Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

I

O

O

II

III

O

IV

O

V

a) I b) II c) III d) IV

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Medium O

11) A correct name for C 6H5 CH2 CH2CH is? a) 3-Benzylpropanone 5

c) 3-Benzylpropanal d) Nonanone e) Nonanal Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

12) What is the correct structure for 3-phenylpropanal? O

O H

O

II

I

III O

H O

IV

V

a) I b) II c) III d) IV

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

6

O

Ph

OH

II

I Ph

III

OH OH

OH

O

OH

O

Ph

O

H

IV

V

O

Ph

a) I b) II d) IV e) V Answer: C 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 e) 4-Methyl-5-chloro-2-benzaldehyde Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

15) What is the correct structure for 4-chloro-3-methylbenzaldehyde? 7

Ph

O

O

H

O

H

H

Cl

II

I Cl

Cl

III

O H H O Cl Cl

IV

V

b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

8

NO2

O

O

H

NO 2

O2N

II

I

O

NO2

NO 2

O O2 N H

O2 N H NO 2

III

IV

O 2N

H

O NO2

V

a) I c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

9

O

O

H

Cl

Cl

I

II O

O

H

H

Cl

IV III

Cl

Cl

O

H

V

a) I b) II c) III e) V Answer: D 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

II

I

III

Br Br

IV

O

V O

10

b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Medium

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

O

a)2-Methyl-2-bromobutanone c)(R)-2-Bromo-2-methylcyclobutanone d) (S)-1-Bromo-1-methyl-2-cyclobutanone e)(R)-1-Bromo-1-methyl-2-cyclobutanone Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

20) What is the correct IUPAC name for the following compound?

a)2-Bromobutanone b)(S)-2-Bromo-cyclobutanone d) (S)-1-Bromo-2-cyclobutanone e)(R)-1-Bromo-2-cyclobutanone Answer:C

11

Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

21) 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 e) (S)-1-chloro-3-cyclohexanone Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

22) What is the correct IUPAC name for the following compound?

a) (S)-3-chloro-1-hexanone b) (S)-1-chloro-3-hexanone d) (S)-3-chlorocyclohexanone e) (S)-1-chloro-3-cyclohexanone Answer:C Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

12

23) What is the correct IUPAC name for the following compound?

a) (1S, 4R)-bicyclo[2.2.1]hexan-2-one b) (1S, 4R)-bicyclo[2.1.2]heptan-2-one d) (1R, 4S)-bicyclo[2.1.1]heptan-2-one e) (1S, 4S)-bicyclo[2.1.2]heptan-2-one Answer:C Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

24) What is the correct IUPAC name for the following compound?

b) bicyclo[1.0.1]butan-2-one c) bicyclo[1.1.0]pentan-2-one d) bicyclo[0.1.1]butan-2-one e) bicyclo[1.0.1]pentan-2-one Answer:A Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

25) What is the correct IUPAC name for the following compound?

13

a) bicyclo[1.1.1]pentan-2-one c) cyclopentanone d) methylenepentan-2-one e) bicyclo[1.0.1]pentan-2-one Answer:B Topic: Nomenclature Section: 16.2 Difficulty Level: Hard O CH3

26) What is the IUPAC name for

CH

CH 2

C

C6 H5

OH

a) 4-Oxo-5-phenyl-2-hexanol c) 2-Hydroxy-5-phenyl-4-hexanone d) 2-Hydroxypropyl-1-phenylethyl ketone e) 5-Hydroxy-3-keto-2-phenylhexane Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

27) Which is the proper name for the structure shown? O2N

CH

O NO2

a) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal b) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal d) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde e) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde Answer: C Topic: Nomenclature 14

CH3

?

Section: 16.2 Difficulty Level: Hard

28) 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

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

29) 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

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

15

Br Br

Br O O

O

II

I

III

Br Br

IV

O

V

O

b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

Br O O

O

II

I

III

Br Br

IV

O

V

a) I b) II d) IV e) V Answer: C 16

O

Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

32) 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 d) (S)-5-Bromo-2-heptanone e) (R)-3-Bromopentyl methyl ketone Answer: C Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

33) 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 e) (R)-3-Bromopentyl methyl ketone Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

17

Br

H

Br

Br

H

H

O

H

O

O

II

I

III

H

Br

H

H

Br

O

O

V IV

a) I c) III d) IV e) V Answer: B Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

35) What is the correct structure for (S)-5-bromo-2-heptanone? Br

H

Br

Br

H

H

H

O

O

II

I

III

H

Br

H

H

Br

O

O

V IV

18

O

a) I b) II c) III d) IV

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

36) 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

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

O

III

O

II

I

O

O

V

IV

a) I b) II c) III

19

O

e) V Answer: D Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

O

III

O

II

I

O

O

V

IV

a) I b) II d) IV e) V Answer: C Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

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

a) I b) II 20

O

c) III d) IV

Answer: E Topic: Nomenclature Section: 16.2 Difficulty Level: Hard

40) 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 c)Butanal d)1-Fluorobutane e)Diethylether Answer: B Topic: Physical Properties, Relationships, Stereochemistry Section: 16.3 Difficulty Level: Easy

41) Stereoisomers can exist in the case of which of the following?

b) The oxime of acetone c) The phenylhydrazone of cyclohexanone d) The cyclic acetal formed from propanal and ethane-1,2-diol e) The imine of cyclopentanone Answer: A Topic: Physical Properties, Relationships, Stereochemistry Section: 16.8 Difficulty Level: Medium

42) Stereoisomers can exist in the case of which of the following? a) The hydrazoneof benzophenone

21

c) The phenylhydrazone of 4-methylcyclohexanone d) The imine of cyclopentanone e) Two of these choices. Answer: B Topic: Physical Properties, Relationships, Stereochemistry Section: 16.8 Difficulty Level: Medium

43) In which of the following reactions is the final product expected to be formed as a racemic mixture? H

a) C6H5 MgBr + C6 H5C

O

O

b) HCN +

CH 3CCH3

H

d) CH 3C

+ xs CH3OH + HCl

O O

CH 3CHCH2COC 2 H5

e)

+ (i-Bu) 2 AlH

CH3

Answer: C Topic: Physical Properties, Relationships, Stereochemistry Section: 16.9 Difficulty Level: Medium

44)Acetals are unstable in the presence of an aqueous solution of which of these?

b) NaOH c) KHCO3 d) Na2CO3 e) NaCl 22

Answer: A Topic: Reagents Section: 16.7 Difficulty Level: Easy

45) 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. d) RCOOH is reduced to RCH3. e) RCOOH is converted into R2C=O. Answer: C Topic: Reagents Section: 16.4 Difficulty Level: Easy

46) Identify the reagent(s) that would bring about the following reaction: CH3CH2CH2COCl ⎯⎯⎯→

CH3CH2CH2CHO

a) H2/Ni b) Li/liq.NH3 d) NaBH4, CH3OH e) LiAlH4, ether Answer: C Topic: Reagents Section: 16.4 Difficulty Level: Easy

47) Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group of an aldehyde or ketone? b) H3O+ 23

c) AlCl3 d) BF3 e) ZnCl2 Answer: A Topic: Reagents Section: 16.6 Difficulty Level: Easy

48) Which reagent(s) could be used to carry out the following transformation? O

?

a) Zn(Hg), HCl, reflux b) LiAlH4, ether c) HSCH2CH2SH, BF3; then Raney Ni (H2) d) All of these choices.

Answer: E Topic: Reagents Section: 16.7 Difficulty Level: Medium

49) The following reduction can be carried out with which reagent(s)?

? O

a) Zn(Hg), HCl b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2) c) H2NNH2, KOH d) None of these choices.

Answer:E Topic: Reagents Section: 16.7 24

Difficulty Level: Medium

50) The following reduction can be carried out with which reagent(s)?

? O

a) Zn(Hg), HCl b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2) c) NaBH4, CH3OH e) Zn(Hg), HCl and NaBH4, CH3OH Answer: D Topic: Reagents Section: 16.7 Difficulty Level: Medium

51) Which reagent will not differentiate between 3-butenal and 2-butanone? a) Br2/CCl4 b) Ag2O,OHd) KMnO4,OHe) None of these choices. Answer: C Topic: Reagents Section: 16.8 Difficulty Level: Medium H

H

52) The compound C6 H5 C N N CC 6H5 is produced by the reaction of an excess of benzaldehyde with which compound? a) Ammonia c) Nitrogen d) Phenylhydrazine e) Hydroxylamine 25

Answer: B Topic: Reagents Section: 16.8 Difficulty Level: Medium

53) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is:

b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl c) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Phd) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph->H e) H > 3° alkyl > 2° alkyl > 1° alkyl > methyl>PhAnswer:A Topic: Mechanisms Section: 16.12 Difficulty Level: Medium

54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound?

O

b) C6 H5COCH3 c) C6H5C(OCH3)3 OH

O

d) C6 H5 CHOCH3 and C 6H5COCH3 O

e) C6 H5COCH3 andC6H5C(OCH3)3 Answer: A Topic: Reaction Products Section: 16.7 Difficulty Level: Easy

55) Select the structure of the major product in the following reaction. 26

i) BH3 ii) H2O2,OH-, H2O

?

a) Ethylbenzene b) 1-Phenylethanol c) Acetophenone e) Vinylbenzene Answer: D Topic: Reaction Products Section: 16.4 Difficulty Level: Medium

56) Select the structure of the major product in the following reaction.

a) I b) II c) III e) V

27

Answer:D Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

57) Select the structure of the major product in the following reaction. O

CH3COOOH

a) I b) II d) IV e) V Answer:C Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

58) Select the structure of the major product in the following reaction.

28

b) II c) III d) IV e) V Answer:A Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

59) Select the structure of the major product in the following reaction.

29

a) I c) III d) IV e) V Answer:B Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

60) Select the structure of the major product in the following reaction.

30

a) I b) II d) IV e) V Answer:C Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

61) Select the structure of the major product in the following reaction.

31

a) I b) II d) IV e) V Answer:C Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

62) Select the structure of the major product in the following reaction.

32

a) I b) II d) IV e) V Answer:C Topic: Reaction Products Section: 16.12 Difficulty Level: Medium

63) Select the structure of the major product in the following reaction.

i) BH3 ii) H2 O 2,OH- , H2O

?

33

OH

O

OH

II

I

III

H

O

IV

V

a) I b) II c) III e) V Answer: D Topic: Reaction Products Section: 16.4 Difficulty Level: Medium

64) What is the final product, Z, of the following synthesis?