Title | Ch17 - Chapter 17 Questions for Boson |
---|---|
Course | Organic Chemistry II |
Institution | The City College of New York |
Pages | 116 |
File Size | 1.5 MB |
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Chapter 17 Questions for Boson...
Package Title: Solomons Test Bank Course Title: Solomons 12e 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 e) Ethyl 3-methylbutanoate 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 d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 1
3) The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is:
a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
2
4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:
a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
3
5) The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is:
a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
4
6) The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is:
a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
5
7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:
a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
6
8) The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is:
a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
7
9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:
a) I b) II c) III d) IV 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 b) 2-Methylbutyl 3-methylbutanoate c) 3-Methylbutyl isovalerate d) Isopentyl isovalerate e) Isopentyl isobutyrate Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
8
11) 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 d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium Cl Cl
12) What is the IUPAC name for
O
a) -Chlorovaleryl chloride b) 2-Chloropentanoyl 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
9
13) The correct structure for ethyl 2-chloropentanoyl chloride is: O O
O Cl
OH Cl
OH
OH
Cl
II
I
III O
Cl
O Cl Cl
IV
V
a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
O
O
14) What is the IUPAC name for a) -Dimethylbutyl acetateb) -Dimethyl-4-oxoethanal c) -Dimethylbutyl methanoate d) -Dimethylbutyl methylate e) -Dimethylbutyl formylate Answer: C Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
10
Cl
15) The correct structure for -methylbutyl methanoate is: O
O
H
H
O
O
O
H
II
I
O
III
O
O
O
O
IV
V
a) I b) II c) III d) IV e) V Answer: C Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
11
16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide? H N
N
N
O
O
I
O
II
N
III
N O
IV
O
V
a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium
12
17) Which of the following structures is 3,4-dimethylpentyl chloroformate? 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 e) V Answer: E Topic: Nomenclature Section: 17.9 Difficulty Level: Hard
18) Which compound would be the strongest acid? a) CHCl2CH2CH2CO2H b) ClCH2CHClCH2CO2H c) CH3CCl2CH2CO2H d) CH3CHClCHClCO2H e) CH3CH2CCl2CO2H Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Easy
13
19) Which compound would be the weakest acid? a) CHCl2CH2CH2CO2H 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 e) 2,2-dichlorobutanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
21) Which compound would be expected to have the lowest pKa? a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e) 2,2-dichlorobutanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
14
22) Which compound would be expected to have the highest pKa? a) 4,4-dichlorobutanoic 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
23) Which compound would be the weakest acid? a) 4,4-dichlorobutanoic 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 b) acetic acid c) ethane d) acetylene e) ethanol Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Medium
15
25) Which compound would be the weakest acid? a) water b) acetic acid c) ethane d) acetylene e) ethanol Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
26) Which compound would be expected to have the highest pKa? a) water b) acetic acid c) ethane d) acetylene e) ethanol Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
27) Which compound would be expected to have the lowest pKa? a) water b) acetic acid c) ethane d) acetylene e) ethanol Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Medium
16
28) In which of the following sequences are the compounds listed in order of decreasing acidity? a) CH3COOH > H2O > CH3CH2OH b) CH3CH2OH > CH3COOH > H2O c) CH3COOH > CH3CH2OH > H2O d) H2O > CH3COOH > CH3CH2OH e) CH3CH2OH > H2O > CH3COOH
> > > > >
HCCH > NH3 HCCH > NH3 NH3 > HCCH HCCH > NH3 HCCH > NH3
Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium
29) In which of the following sequences are the compounds listed in order of increasing acidity? a) NH3 < HCCH < CH3CH2OH < H2O < CH3COOH b) CH3CH2OH < NH3 < H2O < HCCH < CH3COOH c) CH3COOH < CH3CH2OH < H2O < NH3 < HCCH d) H2O < CH3COOH < CH3CH2OH < HCCH < NH3 e) NH3 < H2O < CH3COOH < HCCH < 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 decreasing acidity? a) CH3COOH > H2O > PhOH b) PhOH > CH3COOH > H2O c) CH3COOH > PhOH > H2O d) H2O > CH3COOH > PhOH e) PhOH > H2O > CH3COOH
> > > > >
HCCH HCCH HCCH HCCH HCCH
> > > > >
NH3 NH3 NH3 NH3 NH3
Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
31) In which of the following sequences are the compounds listed in order of decreasing acidity? 17
a) PhCOOH > H2O > PhOH > PhCH2OH > PhH b) PhCOOH > PhOH > H2O > 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 strongest acid? Cl CO2H
CO2H
CO2H Cl
Cl
I
II
III
CO2H Cl
IV
Cl
CO2H Cl
Cl
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
33) Which of the following would be the weakest acid? 18
Cl CO2H
CO2H
CO2H Cl
Cl
I
II
Cl
III
CO2H
CO2H
Cl
Cl
IV
Cl
V
a) I 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 strongest acid? F CO2H
CO2H
CO2H
F
I
III
CO2H F
IV
F
F
II CO2H F
F
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 35) Which of the following would be the strongest acid? 19
F CO2H
CO2H
CO2H
Cl
I
F
F
II
III
CO2H
CO2H
F
Cl
Cl
IV
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
36) Which of the following would be the strongest acid? NO 2 CO2H
CO2H O2 N
I
CO 2H O2N
II
III
CO2 H NO2
IV
NO2
CO2H O2N
NO2
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 37) Which of the following would be the strongest acid? 20
CH 3 CO2H
CO2H H3 C
I
CO2H H 3C
II
CH3
III
CO2 H
CO2H
CH3
H 3C
IV
CH 3
V
a) I 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 strongest acid? CO2H
OCH3 CO2H
CO2H H3CO
I
H3CO
II
III
CO2 H OCH 3
IV
OCH3
CO2H H3CO
OCH 3
V
a) I b) II c) III d) IV e) V Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium 39) Which of the following would be the weakest acid? 21
CO2H
OCH3 CO2H
CO2H H3CO
I
H3CO
II
III
CO2 H OCH 3
OCH3
CO2H H3CO
IV
OCH 3
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium
40) Which of the following would be the weakest acid? CH 3 CO2H
CO2H H3 C
I
CO2H H 3C
II
III
CO2 H CH3
IV
CH3
CO2H H 3C
CH 3
V
a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 41) Which of the following acids would have the smallest value for pKa? 22
a) BrCH2CH2CH2COOH b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH e) BrCCl2CH2CH2COOH Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
42) Which of the following acids would be expected to have the smallest value for pKa? a) 4-bromobutanoic acid b) 4-chlorobutanoic acid c) 4,4-dichlorobutanoic acid d) 4-bromo-4-iodobutanoic acid e) 4-bromo-4,4-dichlorobutanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
43) Which of the following acids would have the largest value for pKa? a) BrCH2CH2CH2COOH b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH e) BrCCl2CH2CH2COOH Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium
44) Which of the following acids would be expected to have the largest value for pKa? 23
a) 4-bromobutanoic acid 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 e) HOOCCH2COOH Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
46) Which compound would be most acidic? 24
O
a)
OH
OH
b)
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 e) None of these choices. 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? 25
a) CH3CO2H > CH3CH2OH > C6H5OH > H2O b) C6H5OH > CH3CO2H > H2O > CH3CH2OH c) CH3CO2H > H2O > C6H5OH > CH3CH2OH d) H2O > CH3CO2H > C6H5OH > CH3CH2OH e) CH3CO2H > C6H5OH > CH3CH2OH > H2O Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium
49) Which of the following would be the strongest acid? a) Benzoic acid b) 4-Nitrobenzoic 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 b) 4-Nitrobenzoic 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? 26
a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: D Topic: Acidity Section: 17.2 Difficulty Level: Hard
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 d) 4-Methoxybenzoic 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 e) 2-Fluoro-4-bromopentanoic 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? 27
a) 2,3-Dimethylhexanoic acid b) 3,3-Diiodopentanoic acid c) 3-Iodo-4-bromopentanoic acid d) 3-Chloro-4-bromohexanoic acid e) 2-Fluoro-4-bromopentanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Hard
55) Which compound would be most acidic? a) Acetic acid 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? a) Acetic acid 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 28
sharp band at 1710 cm-1. Which of these compounds could it be? a) 1-Butanol b) Propyl acetate c) Butanoic acid 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, C 6H12O2. Its IR spectrum shows a strong absorption band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at 1.4 and 2.0. The most likely structure for this compound is: O
O
O
O
O
O
I
II
III
O O
IV
O O
H
V
a) I b) II c) III d) IV e) V Answer: D Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium
59) A compound has the molecular formula, C 6H12O2. Its IR spectrum shows a strong absorption 29
band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at 1.2 and 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 e) V Answer: E Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium
60) A compound has the molecular formula C8H14O4. Its IR spectrum shows a strong absorption 30
band near 1740 cm-1. Its 1H NMR spectrum consists of: triplet, 1.3 singlet, 2.6 quartet, 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
CO2 H
O
O O
IV
V
a) I 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: 31
triplet, 0.90 multiplet, 1.60 singlet, 1.95 triplet, 3.95 The IR spectrum showed a strong absorption band near 1740 cm -1. The most likely structure for the compound is: O O
a)
O O O
b) O
c) H
d)
O O
O 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: 32
singlet, 2.7 singlet, 3.1 multiplet, 7.3 The IR spectrum shows a strong absorption band near 1750 cm-1. The most likely structure for the compound is: O O
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