Exam Questions Carboxylic Acids & Derivatives Chapter 17 13e - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
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?
a) Isobutyl ethanoate
b) Ethyl isopropanoate
c) 3-methylbutyl ethanoate
d) Ethoxy isobutyl ketone
e) Ethyl 3-methylbutanoate
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
2) The correct structure for ethyl 3-methylbutanoate is:
a) I
b) II
c) III
d) IV
e) V
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
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:
a) I
b) II
c) III
d) IV
e) V
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
e) V
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
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:
a) I
b) II
c) III
d) IV
e) V
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
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
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
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
11) The correct structure for ethyl 3-methylbutanoate is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
12) What is the IUPAC name for 
a) -Chlorovaleryl chloride
b) 2-Chloropentanoyl chloride
c) 1-Chloropentanoyl chloride
d) 1,2-Dichloropentanal
e) 1-Chloro-1-butanecarbonyl chloride
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
13) The correct structure for ethyl 2-chloropentanoyl chloride is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
14) What is the IUPAC name for 
a) -Dimethylbutyl acetate-
b) -Dimethyl-4-oxoethanal
c) -Dimethylbutyl methanoate
d) -Dimethylbutyl methylate
e) -Dimethylbutyl formylate
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
15) The correct structure for -methylbutyl methanoate is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
17) Which of the following structures is 3,4-dimethylpentyl chloroformate?
a) I
b) II
c) III
d) IV
e) V
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
Topic: Acidity
Section: 17.2
Difficulty Level: Easy
19) Which compound would be the weakest acid?
a) CHCl2CH2CH2CO2H
b) ClCH2CHClCH2CO2H
c) CH3CCl2CH2CO2H
d) CH3CHClCHClCO2H
e) CH3CH2CCl2CO2H
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
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
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
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
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
25) Which compound would be the weakest acid?
a) water
b) acetic acid
c) ethane
d) acetylene
e) ethanol
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
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
28) In which of the following sequences are the compounds listed in order of decreasing acidity?
a) CH3COOH > H2O > CH3CH2OH > HCCH > NH3
b) CH3CH2OH > CH3COOH > H2O > HCCH > NH3
c) CH3COOH > CH3CH2OH > H2O > NH3 > HCCH
d) H2O > CH3COOH > CH3CH2OH > HCCH > NH3
e) CH3CH2OH > H2O > CH3COOH > HCCH > NH3
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
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 > HCCH > NH3
b) PhOH > CH3COOH > H2O > HCCH > NH3
c) CH3COOH > PhOH > H2O > HCCH > NH3
d) H2O > CH3COOH > PhOH > HCCH > NH3
e) PhOH > H2O > CH3COOH > HCCH > NH3
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
31) In which of the following sequences are the compounds listed in order of decreasing acidity?
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
32) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
33) Which of the following would be the weakest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
34) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
35) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
36) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
37) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
38) Which of the following would be the strongest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
39) Which of the following would be the weakest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
40) Which of the following would be the weakest acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
41) Which of the following acids would have the smallest value for pKa?
a) BrCH2CH2CH2COOH
b) ClCH2CH2CH2COOH
c) Cl2CHCH2CH2COOH
d) ICHBrCH2CH2COOH
e) BrCCl2CH2CH2COOH
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
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
44) Which of the following acids would be expected to have the largest 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
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
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
46) Which compound would be most acidic?
a) 
b) 
c) 
d) 
e) 
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.
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
e) CH3CO2H > C6H5OH > CH3CH2OH > H2O
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
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
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
d) 4-Methoxybenzoic acid
e) 4-Iodobenzoic acid
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
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
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
e) 2-Fluoro-4-bromopentanoic acid
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
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
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
c) Butanoic acid
d) Acetyl chloride
e) Acetic anhydride
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 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:
a) I
b) II
c) III
d) IV
e) V
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 1.2 and 3.6. The most likely structure for this compound is:
a) I
b) II
c) III
d) IV
e) V
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 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:
a) I
b) II
c) III
d) IV
e) V
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, 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:
a) 
b) 
c) 
d) 
e) 
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, 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:
a) 
b) 
c) 
d) 
e) 
Topic: Structure Identification (Spectroscopy)
Section: 17.2
Difficulty Level: Medium
63) What would be the product of the following reaction?
\
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7
Difficulty Level: Easy
64) What is the product of this reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.8
Difficulty Level: Easy
65) Predict the major organic product of the reaction sequence,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.8
Difficulty Level: Medium
66) Predict the major organic product of the reaction sequence,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.8
Difficulty Level: Medium
67) Predict the major organic product of the reaction sequence,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.8
Difficulty Level: Medium
68) The product of the following reaction is:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7
Difficulty Level: Medium
69) What is the product of this reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7
Difficulty Level: Medium
70) What is the reactant of the following reaction sequence?
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2Cl
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Medium
71) Predict the major organic product of the reaction sequence below:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Medium
72) What is the expected product, A, of the following reaction sequence?
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Medium
73) What would be the final organic product of the following reaction?
a) (CH3)3CCO2H
b) (CH3)3CCOCH3
c) (CH3)3CCH2OH
d) (CH3)3COCH3
e) (CH3)3CCO2CH3
Topic: Reaction Products
Section: 12.3 and 17.3
Difficulty Level: Medium
74) What is the expected product, A, of the following reaction sequence?
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Medium
75) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7 and 12.3
Difficulty Level: Medium
76) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4 and 17.7
Difficulty Level: Medium
77) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4 and 17.7
Difficulty Level: Medium
78) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4 and 17.7
Difficulty Level: Medium
79) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.8
Difficulty Level: Medium
80) The product, Z, of the following sequence of reactions is which compound?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3 and 17.7
Difficulty Level: Medium
81) What would be the final product?
a) CH3CH2CH2NH2
b) CH3CH2CONH2
c) CH3CH2CONHCOCH2CH3
d) CH3CH2CN
e) CH3CH2COO-NH4+
Topic: Reaction Products
Section: 17.5 and 17.8
Difficulty Level: Medium
82) What would be the final product of this reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.5 and 17.8
Difficulty Level: Medium
83) What would be the final product?
a) CH3CH2CH2NH2
b) CH3CH2CONH2
c) CH3CH2CONHCOCH2CH3
d) CH3CH2CN
e) CH3CH2COCH3
Topic: Reaction Products
Section: 16.5, 17.5, and 17.8
Difficulty Level: Medium
84) What would be the final product of this reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5, 17.5 and 17.8
Difficulty Level: Medium
85) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Medium
86) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Medium
87) What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5N=C=O?
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Products
Section: 17.9
Difficulty Level: Medium
88) What is the ultimate product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.9
Difficulty Level: Medium
89) Identify the product(s) of the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.10
Difficulty Level: Medium
90) Identify the product(s) of the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.10
Difficulty Level: Medium
91) Identify the product(s) of the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.10
Difficulty Level: Medium
92) Identify the product(s) of the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.10
Difficulty Level: Medium
93) What would be the final organic product of the following reaction?
a) C6H5CO2H
b) C6H5CH3
c) C6H5COOCH3
d) C6H5CHO
e) C6H5CH2OH
Topic: Reaction Products
Sections: 16.4 and 17.13
Difficulty Level: Medium
94) What would be the final organic product of the following reaction?
a) 
b) C6H5CH3
c) C6H5COOCH2CH2OH
d) C6H5CHO
e) C6H5CH2OH
Topic: Reaction Products
Sections: 16.4, 16.7 and 17.13
Difficulty Level: Medium
95) What would be the final organic product of the following reaction?
a)
b) C6H5CH3
c) C6H5COOCH2CH2OH
d) C6H5CHO
e) C6H5CH2OH
Topic: Reaction Products
Sections: 16.4, 16.7 and 17.13
Difficulty Level: Medium
96) What would be the final organic product of the following reaction?
a) C6H5CO2H
b) C6H5CH2CH2NCH3
c) C6H5CH2CH2CN
d) C6H5CH=NCH3
e) C6H5CH2NCH3
Topic: Reaction Products
Sections: 16.4, 16.8 and 17.13
Difficulty Level: Medium
97) What would be the final organic product of the following reaction?
a) C6H5CO2H
b) C6H5CH2CH2NCH3
c) C6H5CH2CH2CN
d) C6H5CH=NCH3
e) C6H5CH2NCH3
Topic: Reaction Products
Sections: 16.4, 16.8 and 17.13
Difficulty Level: Medium
98) Predict the major organic product, P, of the following sequence of reactions:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3 and 17.7
Difficulty Level: Hard
99) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4 and 17.7
Difficulty Level: Hard
100) What would be the final organic product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4 and 17.7
Difficulty Level: Hard
101) What is the expected product, A, of the following reaction sequence?
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
102) What is the expected product, A, of the following reaction sequence?
a) Benzyl formate
b) Phenylacetic acid
c) Benzenesulfonic acid
d) 1-Chloro-1-phenyl acetic acid
e) Dibenzylketone
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
103) What is the expected product, A, of the following reaction sequence?
a) Benzyl formate
b) Phenylacetic acid
c) Benzenesulfonic acid
d) 1-Chloro-1-phenyl acetic acid
e) Dibenzylketone
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
104) What is the expected product, A, of the following reaction sequence?
a) Benzyl formate
b) Phenylacetic acid
c) Benzenesulfonic acid
d) 1-Chloro-1-phenyl acetic acid
e) Dibenzylketone
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
105) What is the reactant of the following reaction sequence?
a) BrCH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OH
d) C6H5CH2CH2COOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
106) What is the reactant of the following reaction sequence?
a) C6H5CH3
b) C6H5CH2COOH
c) C6H5CH2OH
d) C6H5CH2CH2COOH
e) O=C(CH2C6H5)2
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
107) What would be the final product, F, of the following sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
108) What would be the final product, F, of the following sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
109) What would be the final product, F, of the following sequence of reactions?
a) 1-Bromo-2-methyl propane
b) 3-Bromo-3-methylbutanoic acid
c) Butanoic acid
d) 3-Methylbutanoic acid
e) Methyl 2-methylproanoate
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
110) What would be the final product, F, of the following sequence of reactions?
a) 1-Bromo-2-methyl propane
b) 3-Bromo-3-methylbutanoic acid
c) Butanoic acid
d) 3-Methylbutanoic acid
e) Methyl 2-methylproanoate
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
111) What would be the final product, F, of the following sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
112) What would be the final product, F, of the following sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
113) What is the reactant of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
114) What is the reactant of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3
Difficulty Level: Hard
115) What would be the final organic product of the following reaction?
a) 2,2-Dimethylpropanoic acid
b) Methyl 2,2-dimethylpropanoate
c) 2,2-Dimethyl-1-propanol
d) t-Butyl methyl ether
e) 3,3-Dimethyl-2-butanone
Topic: Reaction Products
Section: 12.3 and 17.3
Difficulty Level: Hard
116) What would be the final organic product of the following reaction?
a) 2,2-Dimethylpropanoic acid
b) Methyl 2,2-dimethylpropanoate
c) 2,2-Dimethyl-1-propanol
d) t-Butyl methyl ether
e) 3,3-Dimethyl-2-butanone
Topic: Reaction Products
Section: 12.3 and 17.3
Difficulty Level: Hard
117) What would be the final organic product of the following reaction?
a) C6H5CH2CH2CO2H
b) C6H5CH2CH2NH2
c) C6H5CH2CH(CH3)CN
d) C6H5CH2CH=NH
e) C6H5CH2NH2
Topic: Reaction Products
Section: 16.9 and 17.3
Difficulty Level: Hard
118) What would be the final organic product of the following reaction?
a) C6H5CH2CH2CO2H
b) C6H5CH2CH2NH2
c) C6H5CH2CH(CH3)CN
d) C6H5CH2CH=NH
e) C6H5CH2NH2
Topic: Reaction Products
Section: 16.9 and 17.3
Difficulty Level: Hard
119) What would be the final organic product of the following reaction?
a) (CH3)3CCO2H
b) (CH3)3CCOCH3
c) (CH3)3CCH2OH
d) (CH3)3COCH3
e) (CH3)3CCO2CH3
Topic: Reaction Products
Section: 12.3 and 17.3
Difficulty Level: Hard
120) What is the product of this reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7
Difficulty Level: Hard
121) What is the product of this reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.7
Difficulty Level: Hard
122) What final product, Q, would be obtained via the following reaction sequence?
a) cis-3-Methylcyclopentanol
b) trans-3-Methylcyclopentanol
c) Equal amounts of a) and b)
d) 3-Methylcyclopentanone
e) None of these choices.
Topic: Reaction Products
Section: 17.7
Difficulty Level: Hard
123) (R)-3-Hexanol is subjected to the following sequence of reactions: i) acetyl chloride, pyridine; ii) NaOH(aq), heat. What is(are) the likely final product(s)?
a) (R)-3-Hexanol
b) (S)-2-Hexanol
c) Equal amounts of (R)-3-hexanol and (S)-2-hexanol
d) 2-Hexene (cis and trans)
e) 1-Hexen-2-ol
Topic: Reaction Products
Section: 17.7
Difficulty Level: Hard
124) Predict the final product likely to be obtained when (S)-2-methyl-3-pentanol is subjected to the following sequence of reactions: i) benzoyl chloride; ii) NaOH(aq), heat.
a) (S)-2-methyl-3-pentanol
b) (R)-2-methyl-3-pentanol
c) (±)-2-methyl-3-pentanol
d) 2-Methyl-2-pentene
e) (±)-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts
Topic: Reaction Products
Section: 17.7
Difficulty Level: Hard
125) What would be the final product?
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CH=NCH3
Topic: Reaction Products
Section: 17.8
Difficulty Level: Hard
126) What would be the final product?
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CH=NCH3
Topic: Reaction Products
Section: 17.8
Difficulty Level: Hard
127) What would be the final product?
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CHO
Topic: Reaction Products
Section: 17.8
Difficulty Level: Hard
128) What would be the final product?
a) C6H5CH2CO2Ph
b) C6H5CH2CH2NHPh
c) C6H5CH2COPh
d) C6H5CH2CH(Ph)CN
e) C6H5CH2CH=NPh
Topic: Reaction Products
Section: 17.8
Difficulty Level: Hard
129) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
130) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
131) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
132) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
133) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
134) What is the final product of this sequence of reactions?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 17.3, 17.5 and 17.8
Difficulty Level: Hard
135) N,N-Dimethylbenzamide can be made from which of the following?
a) 
b) 
c) 
d) 
e) More than one of these choices.
Topic: Synthesis
Section: 17.8
Difficulty Level: Medium
136) N,N-Dimethylbenzamide can be made from which of the following?
a)
b)
c) 
d)
e) More than one of these choices.
Topic: Synthesis
Section: 17.8
Difficulty Level: Medium
137) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?
a) 
b) 
c) 
d) All of these choices.
e) Only two of these choices.
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
138) Choose the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl CH3CH2CH2CHO
a) H2/Ni
b) Li/liq. NH3
c) LiAl(OC(CH3)3)3H
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Synthesis
Section: 16.4 and 17.5
Difficulty Level: Medium
139) Choose the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl CH3CH2CH2CHO
a) H2/Ni
b) DIBAL-H
c) LiAl(OC(CH3)3)3H
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Synthesis
Section: 16.4 and 17.5
Difficulty Level: Medium
140) Which of the following compounds is capable of forming a -lactone?
a) 5-Hydroxypentanoic acid
b) Pentanedioic acid
c) 4-Hydroxypentanoic acid
d) 3-Hydroxypentanoic acid
e) 2-Hydroxypentanoic acid
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
141) Which of the following reactions could be used to synthesize ethyl acetate?
a) CH3CH2OH + (CH3CO)2O + pyridine
b) CH3CH2OH + (CH3CO)2O
c) CH3CH2OH + CH3CO2H + H3O+
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
142) Choose the reagent(s) that would bring about the following reaction:
CH3CH2CH2CO2CH3 CH3CH2CH2CHO
a) H2/Ni
b) Li/liq NH3
c) Al(CH2CH(CH3)2)H
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Synthesis
Section: 16.4 and 17.7
Difficulty Level: Medium
143) Which of the following reactions would constitute a reasonable synthesis of propyl acetate?
a) 
b) 
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 17.6 and 17.7
Difficulty Level: Medium
144) Which of the following would serve as a reasonable synthesis of ethyl benzoate?
a) 
b) 
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
145) Which of the following combinations of reagents would not produce an ester?
a) 
b) 
c) 
d) 
e) 
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
146) Choose the reagent(s) that would bring about the following reaction:
CH3CH2CH2COOH CH3CH2CH2CH2OH
a) H2/Ni
b) Li/liq NH3
c) LiAlH[OC(CH3)3]3
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Synthesis
Sections: 12.3 and 17.13
Difficulty Level: Medium
147) Choose the reagent(s) that would bring about the following reaction:
CH3C≡CCH2CO2CH2CH3 CH3C≡CCH2CH2OH
a) H2/Ni
b) Li/liq NH3
c) LiAlH[OC(CH3)3]3
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Synthesis
Sections: 12.3 and 17.13
Difficulty Level: Medium
148) Which of the reactions listed below would serve as a synthesis of acetophenone, C6H5COCH3 ?
a) 
b) 
c) 
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Sections: 15.7, 15.9, and 17.13
Difficulty Level: Medium
149) Which of the following would serve as syntheses of (CH3)3CCO2H?
a) 
b) 
c) 
d) and
e) and
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
150) Which carboxylic acid would decarboxylate when heated to 100–150 C?
a) I
b) II
c) III
d) More than one of these choices
e) None of these choices.
Topic: Synthesis
Section: 17.10
Difficulty Level: Medium
151) Which reactant is unlikely to produce the indicated product upon strong heating?
a) 2,2-Dimethylpropanedioic acid 🡪 2-methylpropanoic acid
b) 2-Ethylpropanedioic acid 🡪 Butanoic acid
c) 2-Methyl-3-oxo-pentanoic acid 🡪 3-Pentanone
d) 2-Methyl-4-oxo-pentanoic acid 🡪 2-Methyl-3-butanone
e) 4-Methyl-3-oxo-heptanoic acid 🡪 3-Methyl-2-hexanone
Topic: Synthesis
Section: 17.10
Difficulty Level: Hard
152) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?
a) 
b)
c) 
d) All of these choices.
e) Only two of these choices.
Topic: Synthesis
Section: 17.3
Difficulty Level: Hard
153) Which of the following would serve as syntheses of (CH3)3CCO2H?
a) 
b)
c)
d) and
e) and
Topic: Synthesis
Section: 17.3
Difficulty Level: Hard
154) Which of the following would serve as syntheses of (CH3)3CCO2H?
a) 
b) 
c) 
d) and
e) and
Topic: Synthesis
Section: 17.3
Difficulty Level: Hard
155) Which of the following would yield (S)-2-butanol?
a) 
b) 
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
156) Which of the reactions listed below would serve as a synthesis of benzyl acetate, CH3CO2CH2C6H5?
a) Benzyl alcohol + acetic anhydride 🡪
b) Benzyl alcohol + acetic acid + H3O+ 🡪
c) Benzyl alcohol + acetyl chloride 🡪
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
157) An acid chloride is prepared from the related carboxylic acid by reaction with which of these?
a) HCl
b) Cl2
c) SOCl2
d) HOCl
e) AlCl3
Topic: Methods and Miscellaneous
Section: 17.5
Difficulty Level: Easy
158) An acid chloride is prepared from the related carboxylic acid by reaction with which of these?
a) PCl3
b) PCl5
c) SOCl2
d) Two of these choices.
e) All of these choices.
Topic: Methods and Miscellaneous
Section: 17.5
Difficulty Level: Easy
159) A nitrile is prepared from the corresponding primary amide by reaction with which of these?
a) HCl
b) Cl2
c) P4O10
d) HOCl
e) AlCl3
Topic: Methods and Miscellaneous
Section: 17.8
Difficulty Level: Easy
160) Which of these combinations will not produce benzoic acid?
a) C6H5CH2OH + KMnO4/OH–/H2O, heat; then H3O+
b) C6H5CH3 + KMnO4/OH–/H2O, heat; then H3O+
c) C6H6 + CO2, high pressure
d) C6H5COCH3 + Cl2/OH–/H2O; then H3O+
e) C6H5COCl + OH/H2O; then H3O+
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
161) Intramolecular dehydration to form a cyclic monoester is most likely to occur when which of the following is heated with acid?
a) CH3CH2CH2CHOHCO2H
b) CH3CH2CHOHCH2CO2H
c) CH3CH2CH2CH2CO2H
d) CH3CHOHCH2CH2CO2H
e) HO2CCH2CH2CO2H
Topic: Methods and Miscellaneous
Section: 17.7
Difficulty Level: Medium
162) - and -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?
a) Anhydrides
b) Cycloalkenes
c) Lactones
d) Lactams
e) Cyclic ketones
Topic: Methods and Miscellaneous
Section: 17.7
Difficulty Level: Medium
163) Which of these combinations will not produce benzoic acid?
a) C6H5CH2OH + KMnO4/OH–/H2O, heat; then H3O+
b) C6H5CH3 + KMnO4/OH–/H2O, heat; then H3O+
c) C6H6 + CO2, high pressure
d) C6H5COCH3 + I2/OH–/H2O; then H3O+
e) C6H5COCl + OH–/H2O; then H3O+
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
164) Which of the following is not a method for preparing butanoic acid?
a) CH3CH2CH2Br + NaCN; then H3O+, reflux
b) CH3CH2CH2MgBr + CO2; then H3O+
c) CH3CH2CH2OH + CO
d) CH3CH2CH2CO2Et + OH–/H2O; then H3O+
e) CH3CH2CH2CH2OH + KMnO4/OH–/H2O/heat; then H3O+
Topic: Methods and Miscellaneous
Section: 17.3 and 17.7
Difficulty Level: Medium
165) Which of the following statements concerning nitriles is incorrect?
a) Nitriles can be hydrolyzed to carboxylic acids.
b) Nitriles can be formed from (many) alkyl halides by nucleophilic substitution by cyanide ion.
c) Nitriles can be reduced with excess lithium aluminum hydride to primary amines, RNH2.
d) Nitriles react with Grignard reagents to form tertiary alcohols.
e) Nitriles can be made by the dehydration of amides.
Topic: Methods and Miscellaneous
Section: 16.5 and 17.8
Difficulty Level: Medium
166) Reasoning by analogy, one would predict that the reaction of carbon disulfide with sec-butylmagnesium bromide should yield which of the following (after acidification)?
a) I
b) II
c) III
d) IV
e) V
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Hard
167) Which of the following will not undergo hydrolysis, whether acid or base is present?
a) CH3COCl
b) CH3CONH2
c) (CH3CO)2O
d) CH3CO2CH2CH3
e) CH3COCH2CH2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
168) Which of these compounds could not be formed by nucleophilic attack by an appropriate reagent on acetyl chloride?
a) CH3CONH2
b) CH3CO2CH2CH3
c) ClCH2COCl
d) CH3CO2H
e) (CH3CO)2O
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
169) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) CH3CO2Na
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
170) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) CH3COCH3
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
171) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) CH3CHO
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
172) Which compound would be least reactive toward nucleophilic acyl addition-elimination?
a) CH3COCH3
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
173) Which compound would be least reactive toward nucleophilic acyl addition-elimination?
a) CH3CHO
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
174) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) Acetone
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
175) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) Acetaldehyde
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
176) Which compound would be least reactive toward nucleophilic acyl addition-elimination?
a) Acetone
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
177) Which compound would be least reactive toward nucleophilic acyl addition-elimination?
a) Acetaldehyde
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
178) Which reagent would serve as the basis for a simple chemical test to distinguish between benzoic acid and benzamide?
a) Cold dilute NaOH
b) Cold dilute NaHCO3
c) Cold concd H2SO4
d) More than one of these choices.
e) None of these choices.
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.2 and 17.11
Difficulty Level: Easy
179) Which reagent would best serve as a basis for a simple chemical test to distinguish between CH3CH2COOH and CH3COOCH3?
a) Concd H2SO4
b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) KMnO4/H2O
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.2 and 17.11
Difficulty Level: Easy
180) Which reagent would best serve as the basis for a simple chemical test to distinguish between C6H5CH=CHCOOH and C6H5CH=CHCH3?
a) Concd. H2SO4
b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) KMnO4/H2O
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.2 and 17.11
Difficulty Level: Easy
181) The relative reactivity of acyl compounds toward nucleophilic acyl addition-elimination is:
a) Amide > ester > acid anhydride > acyl chloride
b) Acyl chloride > ester > acid anhydride > amide
c) Ester > acyl chloride > acid anhydride > amide
d) Acyl chloride > acid anhydride > ester > amide
e) Acid anhydride > acyl chloride > ester > amide
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Easy
182) Alkaline hydrolysis of an ester involves initial attack by hydroxide ion on the carbonyl carbon. The presence of substituents on the aromatic ring of ethyl benzoate may be expected to increase/decrease the rate of hydrolysis of this ester. In what order should the five substituents below be arranged to represent the decreasing order of the rates of hydrolysis when these substituents are present in the para position of the aromatic ring in ethyl benzoate?
a) -NO2 > -H > -Cl > -CH3 > -OCH3
b) -NO2 > -Cl > -H > -CH3 > -OCH3
c) -OCH3 > -CH3 > -Cl > -H > -NO2
d) -Cl > -NO2 > -H > -OCH3 > -CH3
e) -H > -Cl > -CH3 > -OCH3 > -NO2
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.4
Difficulty Level: Medium
183) In which of these species are all the carbon-oxygen bonds of equal length?
a) Diethyl carbonate
b) Methyl butanoate
c) Lithium acetate
d) Propionic anhydride
e) Pentanoic acid
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.2
Difficulty Level: Hard
Question type: fill-in-the-blank
184) While the IUPAC name for HCO2H is methanoic acid, it is commonly known as ___.
Topic: Nomenclature
Section: 17.2
Difficulty Level: Easy
185) Ethanoic acid (CH3CO2H) is usually called ___, from the Latin for “vinegar.”
Topic: Nomenclature
Section: 17.2
Difficulty Level: Easy
Question type: Molecular Drawing
186) Draw the structure for 3-methylbutanoic anhydride.
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
187) Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile.
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
188) Draw the structure for 5-bromo-3-oxohexanoic acid.
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
189) Draw the structure for 4-methylpentyl 3-ethylpentanoate.
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
190) Suggest a structure consistent with the following spectroscopic data:
C5H10O2
IR: 1745 cm−1
1H NMR:
triplet 3H, | 0.90 |
multiplet 2H, | 1.60 |
singlet 3H, | 1.95 |
triplet 2H, | 3.95 |
13C NMR
Broadband decoupled: 10.41, 20.91, 22.14, 66.10, 171.09 δ
DEPT 90: no peaks
DEPT 135: 10.41, 20.91 δ (positive); 22.14, 66.10 δ (negative)
Topic: Structure Identification (Spectroscopy)
Section: 17.2
Difficulty Level: Medium
191) A compound has the formula C7H14O2. The 13C and 1H NMR spectral data for this compound are:
13C NMR
Broadband decoupled 13C NMR: 22.2, 27.7, 32.2, 33.8, 51.4, 174.4 δ
DEPT-90: 27.7 δ
DEPT-135: positive peaks at 22.2, 27.7, 51.4 δ; negative peaks at 32.2, 33.8 δ
1H NMR
0.90 δ, doublet (6H)
1.55 δ, multiplet (3H)
2.30 δ, triplet (2H)
3.67 δ, singlet (3H)
Suggest a structure consistent with this data.
Topic: Structure Identification (Spectroscopy)
Section: 17.2
Difficulty Level: Medium
192) A compound has the formula C6H11BrO2. The 13C and 1H NMR spectral data for this compound are:
13C NMR
Broadband decoupled 13C NMR: 14.2, 27.8, 32.5, 32.6, 60.5, 172.4 δ
DEPT-90: no peaks
DEPT-135: positive peaks at 14.2 δ; negative peaks at 27.8, 32.5, 32.6, 60.5 δ
1H NMR
1.25 δ, triplet (3H)
2.18 δ, multiplet (2H)
2.58 δ, triplet (2H)
3.46 δ, triplet (2H)
4.15 δ, quartet (2H)
Suggest a structure consistent with this data.
Topic: Structure Identification (Spectroscopy)
Section: 17.2
Difficulty Level: Medium
Question type: fill-in-the-blank
193) The presence of electron-withdrawing substituents close to the carboxylic acid functional group will ___ the acidity of the molecule by ___.
Topic: Miscellaneous
Section: 17.2
Difficulty Level: Easy
194) The only carboxylic acid derivative with two carbonyl groups is the ___.
Topic: Miscellaneous
Section: 17.2
Difficulty Level: Easy
195) Cyclic esters are called ___, while cyclic amides are called ___.
Topic: Miscellaneous
Section: 17.7
Difficulty Level: Easy
196) The functional group in a lactam is ___.
Topic: Miscellaneous
Section: 17.8
Difficulty Level: Easy
197) An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol) is called a ___.
Topic: Methods and Miscellaneous
Section: 17.7
Difficulty Level: Easy
198) Base-promoted hydrolysis of esters is sometimes called ___.
Topic: Methods and Miscellaneous
Section: 17.7
Difficulty Level: Easy
199) Litmus paper turns ___ when an aqueous solution of a carboxylic acid is dropped on it.
Topic: Methods and Miscellaneous
Section: 17.11
Difficulty Level: Easy
200) The linkages that join amino acids together to form proteins are primarily ___ bonds.
Topic: Methods and Miscellaneous
Section: 17.2
Difficulty Level: Easy
Question type: Essay
201) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom. For the following reaction, which of these two procedures would be the process of choice and why?
Topic: Reaction Sequence and Mechanistic Pathways
Section: 17.3
Difficulty Level: Medium
202) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom. For the following reaction, which of these two procedures would be the process of choice and why?
Topic: Reaction Sequence and Mechanistic Pathways
Section: 17.3
Difficulty Level: Medium
203) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom. For the following reaction, which of these two procedures would be the process of choice and why?
Topic: Reaction Sequence and Mechanistic Pathways
Section: 17.3
Difficulty Level: Medium
204) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom. For the following reaction, which of these two procedures would be the process of choice and why?
Topic: Reaction Sequence and Mechanistic Pathways
Section: 17.3
Difficulty Level: Medium
205) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom. For the following reaction, which of these two procedures would be the process of choice and why?
Topic: Reaction Sequence and Mechanistic Pathways
Section: 17.3
Difficulty Level: Medium
Question type: fill-in-the-blank
206) Acyl compounds tend to react by acyl substitution mechanisms because they all have a good or reasonably good ___ attached to the carbonyl carbon.
Topic: Reaction Mechanisms
Section: 17.4
Difficulty Level: Easy
207) When a gamma-hydroxy acid is treated with dilute acid, cyclization occurs, producing a ___.
Topic: Reactions
Section: 17.7
Difficulty Level: Easy
Question type: Molecular Drawing
208) Complete the following reaction sequence, giving details of all significant intermediates.
Topic: Reaction Sequence
Section: 12.8 and 17.7
Difficulty Level: Medium
209) Suggest a suitable synthetic strategy for the transformation of 3-methyl-1-pentanol into propyl 3-methylpentanoate
Topic: Reaction Sequence
Section: 17.3 and 17.7
Difficulty Level: Medium
210) Complete the following reaction sequence, giving details of all significant intermediates.
Topic: Reaction Sequence
Section: 17.5 and 17.8
Difficulty Level: Medium
211) Complete the following reaction sequence, giving details of all significant intermediates.
Topic: Reaction Sequence
Section: 17.9
Difficulty Level: Medium
212) Complete the following reaction sequence, giving details of all significant intermediates.
Topic: Reaction Sequence
Section: 12.3, 17.3 and 17.7
Difficulty Level: Hard
213) Given a mixture of benzyl alcohol, phenol, and benzoic acid dissolved in ether, outline in a flow diagram an extraction method to separate each.
Topic: Physical Properties, Isolation
Section: 17.2 and 17.11
Difficulty Level: Medium
214) The pKa of benzoic acid is 4.20. A benzoic acid substituted in the para-position with some group G (shown below) is reported to have a pKa of 3.92.
Based on this information is group G an electron withdrawing or electron donating group?
Topic Acidity
Section 17.2
Difficulty Level: Medium
215) Nylon 12 is a polyamide that has found significant commercial value in the manufacture of automobile fuel lines. Nylon 12 is prepared industrially through the polymerization of the 13-member ring lactam monomer shown:
This lactam is readily prepared by the reaction of the cyclododecanone oxime with aqueous acid.
Propose a mechanism for this transformation.
Topic: Mechanisms
Section: 17.8
Difficulty Level: Hard
216) Which compound would be least acidic?
a)
b)
c)
d)
e)
Topic: Acidity
Section: 17.2
Difficulty Level: Medium
217) Which compound would be least acidic?
a) Acetic acid
b) Ethanol
c) Phenol
d) Acetone
e) Water
Topic: Acidity
Section: 17.2
Difficulty Level: Hard
218) Which of the following acids would be expected to have the largest value for pKa?
a) Acetic acid
b) Ethanol
c) Phenol
d) Acetone
e) Water
Topic: Acidity
Section: 17.2
Difficulty Level: Hard
219) What is the major product of the following reaction?
a) N,N-dimethylbenzamide
b) benzoic acid
c) methyl benzoate
d) benzamide
e) benzyl alcohol
Topic: Synthesis
Section: 17.8
Difficulty Level: Medium
220) What is the major product of the following reaction?
a) N,N-dimethylbenzamide
b) benzoic acid
c) methyl benzoate
d) benzamide
e) benzyl alcohol
Topic: Synthesis
Section: 17.8
Difficulty Level: Medium
221) What is the major product of the following reaction?
a) N,N-dimethylbenzamide
b) benzoic acid
c) methyl benzoate
d) benzamide
e) benzyl alcohol
Topic: Synthesis
Section: 17.8
Difficulty Level: Medium
222) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) 3,3-dimethylbutanoic acid
d) 3-methylbutene
e) 3-methyl-2-butene
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
223) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) 3,3-dimethylbutanoic acid
d) 3-methylbutene
e) 3-methyl-2-butene
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
224) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) 3,3-dimethylbutanoic acid
d) 3-methylbutene
e) 3-methyl-2-butene
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
225) What is the major product of the following reaction?
a) propyl acetate
b) ethyl acetate
c) propyl propanoate
d) methyl methanoate
e) ethyl methanoate
Topic: Synthesis
Section: 17.6 and 17.7
Difficulty Level: Medium
226) What is the major product of the following reaction?
a) propyl acetate
b) ethyl acetate
c) propyl propanoate
d) methyl methanoate
e) ethyl methanoate
Topic: Synthesis
Section: 17.6 and 17.7
Difficulty Level: Medium
227) What is the major product of the following reaction?
a) propyl acetate
b) ethyl acetate
c) ethyl propanoate
d) propyl propanoate
e) ethyl methanoate
Topic: Synthesis
Section: 17.6 and 17.7
Difficulty Level: Medium
227) What is the major product of the following reaction?
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
229) What is the major product of the following reaction?
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
230) What is the major product of the following reaction?
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
231) What is the major product of the following reaction?
a) ethyl acetate
b) methyl acetate
c) iso-propyl acetate
d) propyl acetate
e) ethyl 2-methylpropanoate
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
232) What is the major product of the following reaction?
a) ethyl acetate
b) methyl acetate
c) iso-propyl acetate
d) propyl acetate
e) ethyl 2-methylpropanoate
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
233) What is the major product of the following reaction?
a) ethyl acetate
b) methyl acetate
c) iso-propyl acetate
d) propyl acetate
e) ethyl 2-methylpropanoate
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
234) What is the major product of the following reaction?
a) ethyl acetate
b) methyl acetate
c) iso-propyl acetate
d) propyl acetate
e) ethyl 2-methylpropanoate
Topic: Synthesis
Section: 17.7
Difficulty Level: Medium
235) What is the major product of the following reaction?
a) acetophenone
b) ethylbenzene
c) benzyl alcohol
d) phenol
e) ethyl phenyl ether
Topic: Synthesis
Sections: 15.7, 15.9, and 17.13
Difficulty Level: Medium
236) What is the major product of the following reaction?
a) acetophenone
b) ethylbenzene
c) benzyl alcohol
d) phenol
e) ethyl phenyl ether
Topic: Synthesis
Sections: 15.7, 15.9, and 17.13
Difficulty Level: Medium
237) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
238) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
239) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
240) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
241) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
242) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
243) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
244) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
245) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
246) What is the major product of the following reaction?
a) 2,2-dimethylpropanoic acid
b) 2-methylpropene
c) methyl 2,2-dimethylpropanoate
d) tert-butyl aceate
e) methyl tert-butyl ether
Topic: Synthesis
Section: 17.3
Difficulty Level: Medium
247) What is the major product of the following reaction?
a) (S)-2-butanol
b) (R)-2-butanol
c) (S)-sec-butyl acetate
d) (R)-sec-butyl acetate
e) 2-butanol
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
248) What is the major product of the following reaction?
a) (S)-2-butanol
b) (R)-2-butanol
c) (S)-sec-butyl acetate
d) (R)-sec-butyl acetate
e) 2-butanol
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
249) What is the major product of the following reaction?
a) (S)-2-butanol
b) (R)-2-butanol
c) (S)-sec-butyl acetate
d) (R)-sec-butyl acetate
e) 2-butanol
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
250) What is the major product of the following reaction?
Benzyl alcohol + acetic anhydride 🡪
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
251) What is the major product of the following reaction?
Benzyl alcohol + acetic acid + H3O+ 🡪
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
252) What is the major product of the following reaction?
Benzyl alcohol + acetyl chloride 🡪
a) ethyl benzoate
b) benzyl acetate
c) phenyl acetate
d) ethylbenzene
e) ethyl phenyl ether
Topic: Synthesis
Section: 17.7
Difficulty Level: Hard
253) What is the major product of the following reaction?
C6H5CH2OH + KMnO4/OH–/H2O, heat; then H3O+
a) benzaldehyde
b) toluene
c) benzyl alcohol
d) phenol
e) benzoic acid
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
254) What is the major product of the following reaction?
C6H5CH3 + KMnO4/OH–/H2O, heat; then H3O+
a) benzaldehyde
b) toluene
c) benzyl alcohol
d) phenol
e) benzoic acid
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
255) What is the major product of the following reaction?
C6H5COCH3 + Cl2/OH–/H2O; then H3O+
a) benzaldehyde
b) toluene
c) benzyl alcohol
d) phenol
e) benzoic acid
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
256) What is the major product of the following reaction?
C6H5COCl + OH/H2O; then H3O+
a) benzaldehyde
b) toluene
c) benzyl alcohol
d) phenol
e) benzoic acid
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
257) What is the major product of the following reaction?
C6H5COCH3 + I2/OH–/H2O; then H3O+
a) benzaldehyde
b) toluene
c) benzyl alcohol
d) phenol
e) benzoic acid
Topic: Methods and Miscellaneous
Section: 17.3
Difficulty Level: Medium
258) What is the major product of the following reaction?
CH3CH2CH2Br + NaCN; then H3O+, reflux
a) 2-pentanone
b) butanoic acid
c) ethyl butanoate
d) butanol
e) dibutyl ether
Topic: Methods and Miscellaneous
Section: 17.3 and 17.7
Difficulty Level: Medium
259) What is the major product of the following reaction?
CH3CH2CH2MgBr + CO2; then H3O+
a) 2-pentanone
b) butanoic acid
c) ethyl butanoate
d) butanol
e) dibutyl ether
Topic: Methods and Miscellaneous
Section: 17.3 and 17.7
Difficulty Level: Medium
260) What is the major product of the following reaction?
CH3CH2CH2CO2Et + OH–/H2O; then H3O+
a) 2-pentanone
b) butanoic acid
c) ethyl butanoate
d) butanol
e) dibutyl ether
Topic: Methods and Miscellaneous
Section: 17.3 and 17.7
Difficulty Level: Medium
261) What is the major product of the following reaction?
CH3CH2CH2CH2OH + KMnO4/OH–/H2O/heat; then H3O+
a) 2-pentanone
b) butanoic acid
c) ethyl butanoate
d) butanol
e) dibutyl ether
Topic: Methods and Miscellaneous
Section: 17.3 and 17.7
Difficulty Level: Medium