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Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 17

Question type: Multiple choice

1) Which of the following is the best name for the following compound? O O

a) Isobutyl ethanoate b) Ethyl isopropanoate c) 3-methylbutyl ethanoate d) Ethoxy isobutyl ketone

Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

2) The correct structure for ethyl 3-methylbutanoate is: O

O

O

O

O

O

II

I

III

O

O

O

O

IV

V

a) I b) II c) III e) V 1

Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

3) The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is:

a) I b) II c) III e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:

2

a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

5) The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is:

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

Answer: E 3

Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

6) The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is:

a) I b) II c) III e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:

4

a) I c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

8) The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is:

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

Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:

5

a) I b) II c) III e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium O O

10) A correct name for

is:

a) 2-Methylbutyl 2-methylbutanoate c) 3-Methylbutyl isovalerate d) Isopentyl isovalerate e) Isopentyl isobutyrate Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

11) The correct structure for ethyl 3-methylbutanoate is:

6

O

O

O

O

O

O

II

I

III

O

O

O

O

IV

V

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

Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium Cl Cl

12) What is the IUPAC name for

O

a) ∝-Chlorovaleryl chloride c) 1-Chloropentanoyl chloride d) 1,2-Dichloropentanal e) 1-Chloro-1-butanecarbonyl chloride Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

13) The correct structure for ethyl 2-chloropentanoyl chloride is:

7

O O

O Cl

OH

OH

OH

Cl Cl

II

I

III O

Cl

O Cl Cl

IV

V

Cl

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

Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

O

O

14) What is the IUPAC name for a) 2,3−Dimethylbutyl acetate b) 2,3−Dimethyl-4-oxoethanal d) 2,3−Dimethylbutyl methylate e) 2,3−Dimethylbutyl formylate Answer: C Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

15) The correct structure for ethyl 2,3−dimethylbutyl methanoate is: 8

O

O

H

O

H

O

O

H

O

II

I

III

O

O

O

O

IV

V

b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 17.2 Difficulty Level: Medium

16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide? H N

N

O

N

O

I

O

II

N

III

N O

IV

O

V

a) I b) II c) III d) IV 9

Answer: E Topic: Nomen clature Section: 17.2 Difficulty Level: Medium

17) Which of the following structures is 3,4-dimethylpentyl chloroform ate? H

Cl

O O

O

Cl

O

Cl

I

O O

II O O

III Cl

Cl

IV

O O

V

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

Answer: E Topic: Nomen clature Section: 17.9 Difficulty Level: Hard

18) Which compound would be the strongest acid? a) CHCl2CH2CH2CO2H b) ClCH2CHClCH2CO2H c) CH3CCl2CH2CO2H d) CH3CHClCHClCO2H Answer: E Topic: Acidity Section: 17.2 10

Difficulty Level: Easy

19) Which compound would be the weakest acid?

b) ClCH2CHClCH2CO2H c) CH3CCl2CH2CO2H d) CH3CHClCHClCO2H e) CH3CH2CCl2CO2H Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Easy

20) Which compound would be the strongest acid? a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium

21) Which compound would be expected to have the lower pKa? a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 11

22) Which compound would be expected to have the higher pKa?

b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e) 2,2-dichlorobutanoic acid Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

23) Which compound would be the weakest acid?

b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e) 2,2-dichlorobutanoic acid Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

24) Which compound would be the strongest acid? a) water c) ethane d) acetylene e) ethanol Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Medium

12

25) Which compound would be the weakest acid? a) water b) acetic a cid d) acetylene e) ethanol Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

26) Which compound would be expected to have the higher pKa? a) water b) acetic a cid d) acetylene e) ethanol Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

27) Which compound would be expected to have the lower pKa? a) water c) ethane d) acetylene e) ethanol Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Medium

13

28) In which of the following sequences are the compounds listed in order of

b) CH3CH2OH > CH3COOH > H2O c) CH3COOH > CH3CH2OH > H2O d) H2O > CH3COOH > CH3CH2OH e) CH3CH2OH > H2O > CH3COOH

> > > >

HC≡CH > NH3 NH3 > HC≡CH HC≡CH > NH3 HC≡CH > NH3

Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

29) In which of the following sequences are the compounds listed in order o

b) CH3CH2OH < NH3 < H2O < HC≡CH < CH3COOH c) CH3COOH < CH3CH2OH < H2O < NH3 < HC≡CH d) H2O < CH3COOH < CH3CH2OH < HC≡CH < NH3 e) NH3 < H2O < CH3COOH < HC≡CH < CH3CH2OH Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

30) In which of the following sequences are the compounds listed in order of a) CH3COOH > H2O > PhOH > HC≡CH > NH3 b) PhOH > CH3COOH > H2O > HC≡CH > NH3 3

d) H2O > CH3COOH > PhOH > HC≡CH > NH3 e) PhOH > H2O > CH3COOH > HC≡CH > NH3 Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

14

31) In which of the following sequences are the compounds listed in order of a) PhCOOH > H2O > PhOH > PhCH2OH > PhH c) PhH > H2O > PhOH > PhCH2OH > PhCOOH d) PhOH > H2O > PhCOOH > PhCH2OH > PhH e) PhCOOH > H2O > PhOH > PhH > PhCH2OH Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Medium

32) Which of the following would be the Cl CO2H

CO2H

CO2H

Cl

I

Cl

II

III

CO2H Cl

IV

Cl

CO2H Cl

Cl

V

a) I b) II d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

33) Which of the following would be the weakest acid?

15

Cl CO2H

CO2H

CO2H Cl

I

Cl

II

Cl

III

CO2H

CO2H

Cl

Cl

IV

Cl

V

b) II c) III d) IV e) V Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

34) Which of the following would be the F CO2H

CO2H

CO 2H

F

I

F

II CO2 H F

IV

F

III CO2H F

F

V

a) I b) II d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

16

35) Which of the following would be the F CO2H

CO2H

CO 2H

Cl

I

F

II

F

III

CO2 H

CO2H

F

Cl

IV

Cl

V

a) I b) II d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

36) Which of the following would be the NO 2 CO2H

CO 2H

CO2H O2N

O2N

I

II

III

CO2 H NO2

IV

NO 2

CO2H O2 N

NO2

V

a) I b) II d) IV e) V Answer: C Topic: Acidity Section: 17.2 17

Difficulty Level: Medium

37) Which of the following would be the CH 3 CO2H

CO 2H

CO2H H 3C

H3C

I

II

CH 3

III

CO2 H

CO2H H3 C

CH3

IV

CH3

V

b) II c) III d) IV e) V Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

38) Which of the following would be the CO2H

OCH3 CO 2H

CO2H H3CO

H3CO

I

II

III

CO2 H OCH3

IV

OCH 3

CO2H H 3CO

OCH3

V

b) II c) III d) IV e) V Answer: A

18

Topic: Acidity Section: 17.2 Difficulty Level: Medium

39) Which of the following would be the CO2H

OCH3 CO 2H

CO2H H3CO

I

H3CO

II CO2 H OCH3

OCH 3

III CO2H

H 3CO

IV

OCH3

V

a) I b) II d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

40) Which of the following would be the CH 3 CO2H

CO 2H

CO2H H 3C

H3C

I

II

III

CO2 H CH3

IV

CH 3

CO2H H3 C

CH3

V

a) I b) II d) IV e) V

19

Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium

41) Which of the following acids would have the a) BrCH2CH2CH2COOH b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium

42) Which of the following acids would be expected to have the a) 4-bromobutanoic acid b) 4-chlorobutanoic acid c) 4,4-dichlorobutanoic acid d) 4-bromo-4-iodobutanoic acid

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium

43) Which of the following acids would have the

b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH e) BrCCl2CH2CH2COOH Answer: A 20

Topic: Acidity Section: 17.2 Difficulty Level: Medium

44) Which of the following acids would be expected to have the largest value for pKa?

b) 4-chlorobutanoic acid c) 4,4-dichlorobutanoic acid d) 4-bromo-4-iodobutanoic acid e) 4-bromo-4,4-dichlorobutanoic acid Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

45) Which of the following acids would have the smallest value for pKa1? a) HOOCCH2CH2CH2CH2CH2COOH b) HOOCCH2CH2CH2CH2COOH c) HOOCCH2CH2CH2COOH d) HOOCCH2CH2COOH

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium

46) Which compound would be

b)

OH

21

OH

c) O

d) O

e)

H

H

Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium

47) In which of the following are the compounds listed in order of decreasing acidity? a) CH3CO2H > CH3CH2OH > C6H5OH > H2O b) C6H5OH > CH3CO2H > H2O > CH3CH2OH c) CH3CO2H > H2O > C6H5OH > CH3CH2OH d) H2O > CH3CO2H > C6H5OH > CH3CH2OH Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium

48) In which of the following are the compounds listed in order of decreasing acidity? a) CH3CO2H > CH3CH2OH > C6H5OH > H2O b) C6H5OH > CH3CO2H > H2O > CH3CH2OH c) CH3CO2H > H2O > C6H5OH > CH3CH2OH d) H2O > CH3CO2H > C6H5OH > CH3CH2OH

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 22

49) Which of the following would be the strongest acid? a) Benzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Hard

50) Which of the following acids would be expected to have the smallest value for pKa? a) Benzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Hard

51) Which of the following would be the weakest acid? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid e) 4-Iodobenzoic acid Answer: D Topic: Acidity Section: 17.2 Difficulty Level: Hard

23

52) Which of the following acids would be expected to have the largest value for pKa? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid e) 4-Iodobenzoic acid Answer: D Topic: Acidity Section: 17.2 Difficulty Level: Hard

53) Which of the following would be the strongest acid? a) 2,3-Dimethylhexanoic acid b) 3,3-Diiodopentanoic acid c) 3-Iodo-4-bromopentanoic acid d) 3-Chloro-4-bromohexanoic acid

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Hard

54) Which of the following acids would be expected to have the smallest value for pKa? a) 2,3-Dimethylhexanoic acid b) 3,3-Diiodopentanoic acid c) 3-Iodo-4-bromopentanoic acid d) 3-Chloro-4-bromohexanoic acid

Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Hard

55) Which compound would be most acidic? 24

b) Ethanol c) Phenol d) Acetone e) Water Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Hard

56) Which of the following acids would be expected to have the smallest value for pKa? b) Ethanol c) Phenol d) Acetone e) Water Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Hard 57) The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm-1 and a sharp band at 1710 cm-1. Which of these compounds could it be? a) 1-Butanol b) Propyl acetate d) Acetyl chloride e) Acetic anhydride Answer: C Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Easy

58) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption 25

band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at δ 1.4 and δ 2.0. The most likely structure for this compound is: O

O

O

O

O

O

I

II

III

O

O

O

O

IV

H

V

a) I b) II c) III e) V Answer: D Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium

59) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at δ 1.2 and δ 3.6. The most likely structure for this compound is: O

O

O

O

O

O

I

II

III

O

O

O O

IV

V

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

Answer: E Topic: Structure Identification (Spectroscopy) 26

Section: 17.2 Difficulty Level: Medium

60) A compound has the molecular formula C8H14O4. Its IR spectrum shows a strong absorption band near 1740 cm-1. Its 1H NMR spectrum consists of: triplet, δ 1.3 singlet, δ 2.6 quartet, δ 4.2 The most likely structure for the compound is: O O

O O

I

O

O

O

O

O

O

O

O

II

III O

HO2C

CO2H

O

O O

IV

V

b) II c) III d) IV e) V Answer: A Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium 61) A compound with the molecular formula C5H10O2 gave the following 1H NMR spectrum: triplet, δ 0.90 multiplet, δ 1.60 singlet, δ 1.95 triplet, δ 3.95 The IR spectrum showed a strong absorption band near 1740 cm-1. The most likely structure for the compound is:

27

O O O

b) O

c) H

O O O

d)

HO

e) Answer: A Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium 62) A compound with the molecular formula C18H18O4 has a 1H NMR spectrum that consists of: singlet, δ 2.7 singlet, δ 3.1 multiplet, δ 7.3 The IR spectrum shows a strong absorption band near 1750 cm-1. The most likely structure for the compound is: O O

C6 H5

O

C 6H 5

O

a) O

b) C6H5

O

O

O

C6 H5

O C

O C6 H5

O

O

C6 H5

O

d) O C6 H5

O

e)

C 6 H5

O O

Answer: C Topic: Structure Identification (Spectroscopy) 28

Section: 17.2 Difficulty Level: Medium

63) What would be the product of the following reaction? 18 OH O HA ? +

H

O 18 O

18 O

O

O

18O

I

II

18 O

III

O

O

O

18

O

O

II

III

\

a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Easy

64) What is the product of this reaction? O