Ch17-Pilihan Ganda Asam Karboksilat Dan Turunannya

Chapter Seventeen
MULTIPLE CHOICE QUESTIONS
Topic: Acidity
Section: 17.2
Difficulty Level: Easy
1. Which compound would be the strongest acid?

A) CHCl2CH2CH2CO2H
B) ClCH2CHClCH2CO2H
C) CH3CCl2CH2CO2H
D) CH3CHClCHClCO2H
E) CH3CH2CCl2CO2H
Ans:
Topic: Acidity
Section: 17.2
2. Which compound would be the weakest acid?

A) CHCl2CH2CH2CO2H
B) ClCH2CHClCH2CO2H
C) CH3CCl2CH2CO2H
D) CH3CHClCHClCO2H
E) CH3CH2CCl2CO2H
Ans:
1289
Topic: Structure Identification (Spectroscopy)
Section: 17.2
3. 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
Ans:
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
4. 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
Ans:
1290
Topic: Nomenclature
Section: 17.2
5. The correct structure for ethyl 3-methylbutanoate 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
Ans:
1291
Topic: Nomenclature
Section: 17.2
6 O
.
O
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
Ans:
Topic: Nomenclature
Section: 17.2
7. The correct structure for ethyl 2-methylbutyl 3-methylbutanoate 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
Ans:
1292
Topic: Nomenclature
Section: 17.2
8. Cl
Cl
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
Ans:
Topic: Nomenclature
Section: 17.2
9. The correct structure for ethyl 2-chloropenanoyl chloride is:

O
O O
OH Cl
Cl OH OH
Cl
I II III
O
Cl O
Cl
Cl
Cl
IV V
A. I
B. II
C. III
D. IV
E. V
Ans:
1293
Topic: Nomenclature
Section: 17.2
10.
O O
What is the IUPAC name for
A) Dimethylbutyl acetate
B) Dimethyl-4-oxoethanal
C) Dimethylbutyl methanoate
D) Dimethylbutyl methylate
E) Dimethylbutyl formylate
Ans:
Topic: Nomenclature
Section: 17.2
11. The correct structure for ethyl dimethylbutyl methanoate is:

O O O
H O H O H O
I II III
O O
O O
IV V
A. I
B. II
C. III
D. IV
E. V
Ans:
1294
Topic: Nomenclature
Section: 17.2
12. Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?
H
N N N
O O O
I II III
N N
O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1295
Topic: Acidity
Section: 17.2
13. In which of the following sequences are the compounds listed in order of decreasing
acidity?
A) CH3COOH > H2O > CH3CH2OH > HCCH > NH3
B) CH3CH2OH > CH3COOH > H2O > HCCH > NH3
C) CH3COOH > CH3CH2OH > H2O > NH3 > HCCH
D) H2O > CH3COOH > CH3CH2OH > HCCH > NH3
E) CH3CH2OH > H2O > CH3COOH > HCCH > NH3
Ans:
Topic: Acidity
Section: 17.2
14. In which of the following sequences are the compounds listed in order of increasing
acidity?
A) NH3 < HCCH < CH3CH2OH < H2O < CH3COOH
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
Ans:
1296
Topic: Acidity
Section: 17.2
acidity?
A) CH3COOH > H2O > PhOH > HCCH > NH3
B) PhOH > CH3COOH > H2O > HCCH > NH3
C) CH3COOH > PhOH > H2O > HCCH > NH3
D) H2O > CH3COOH > PhOH > HCCH > NH3
E) PhOH > H2O > CH3COOH > HCCH > NH3
Ans:
Topic: Acidity
Section: 17.2
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
Ans:
1297
Topic: Acidity
Section: 17.2
17. Which of the following would be the strongest acid?

Cl
CO2H CO2H CO2H
Cl Cl Cl
I II III
CO2H CO2H
Cl Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Acidity
Section: 17.2
18. Which of the following would be the weakest acid?

Cl
CO2H CO2H CO2H
Cl Cl Cl
I II III
CO2H CO2H
Cl Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1298
Topic: Acidity
Section: 17.2

F
CO2H CO2H CO2H
F F F
I II III
CO2H CO2H
F F F
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Acidity
Section: 17.2

F
CO2H CO2H CO2H
Cl F F
I II III
CO2H CO2H
F Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1299
Topic: Acidity
Section: 17.2

NO2
CO2H CO2H CO2H
O2N O2N NO2

I II III
CO2H CO2H
NO2 O2N NO2

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Acidity
Section: 17.2

CH3
CO2H CO2H CO2H
H3C H3C CH3

I II III
CO2H CO2H
CH3 H3C CH3

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1300
Topic: Acidity
Section: 17.2

OCH3
CO2H CO2H CO2H
H3CO H3CO OCH3

I II III
CO2H CO2H
OCH3 H3CO OCH3

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Acidity
Section: 17.2

OCH3
CO2H CO2H CO2H
H3CO H3CO OCH3

I II III
CO2H CO2H
OCH3 H3CO OCH3

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1301
Topic: Acidity
Section: 17.2

CH3
CO2H CO2H CO2H
H3C H3C CH3

I II III
CO2H CO2H
CH3 H3C CH3

IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Topic: Acidity
Section: 17.2
26. Which of the following acids would have the smallest value for pKa?
A) BrCH2CH2CH2COOH
B) ClCH2CH2CH2COOH
C) Cl2CHCH2CH2COOH
D) ICHBrCH2CH2COOH
E) BrCCl2CH2CH2COOH
Ans:
1302
Topic: Acidity
Section: 17.2
27. Which of the following acids would have the largest value for pKa?
A) BrCH2CH2CH2COOH
B) ClCH2CH2CH2COOH
C) Cl2CHCH2CH2COOH
D) ICHBrCH2CH2COOH
E) BrCCl2CH2CH2COOH
Ans:
Topic: Acidity
Section: 17.2
28. Which of the following acids would have the smallest value for pKa1?
A) HOOCCH2CH2CH2CH2CH2COOH
B) HOOCCH2CH2CH2CH2COOH
C) HOOCCH2CH2CH2COOH
D) HOOCCH2CH2COOH
E) HOOCCH2COOH
Ans:
1303
Topic: Acidity
Section: 17.2
29. Which compound would be most acidic?
A) O
OH
B)
OH
C) OH
D) O
E) O
H H
Ans:
Topic: Acidity
Section: 17.2
30. 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 the above
Ans:
1304
Topic: Acidity
Section: 17.2
31. 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
Ans:
Section: 17.2
32. 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:
O
O O
O
O O
I II III
O O
O O H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1305
Section: 17.2
33. 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:
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
Ans:
1306
Section: 17.2
34. 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:

O O
O O
O O
O O
O O
O O
I II III
O
HO2C O
CO2H O
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1307
Section: 17.2
35. 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) O
O
B) O
O
C) O
O
D) H O
O
E) O
HO
Ans:
1308
Section: 17.2
36. 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) O
O C6H5
C6H5 O
O
B) O O
C6H5
C6H5 O O
C) O
O C6H5
C6H5 O
O
D) O
O C6H5
C6H5 O
O
E) O
O C6H5
C6H5 O
O
Ans:
1309
Topic: Acidity
Section: 17.2
Difficulty Level: Hard

A) Benzoic acid
B) 4-Nitrobenzoic acid
C) 4-Methylbenzoic acid
D) 4-Methoxybenzoic acid
E) 4-Iodobenzoic acid
Ans:
Topic: Acidity
Section: 17.2

A) Benzoic acid
B) 4-Nitrobenzoic acid
C) 4-Methylbenzoic acid
D) 4-Methoxybenzoic acid
E) 4-Iodobenzoic acid
Ans:
1310
Topic: Acidity
Section: 17.2

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
Ans:
Topic: Acidity
Section: 17.2
40. Which compound would be most acidic?
A) Acetic acid
B) Ethanol
C) Phenol
D) Acetone
E) Water
Ans:
1311
Topic: Chemical Tests, Relative Reactivities, and Physical Properties
Section: 17.2
41. 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
Ans:
Topic: Reaction Products
Section: 17.3
42. What is the reactant of the following reaction sequence?
OH
i. Mg/ether
?
ii. CO2
iii. H+ O
A) HCO2CH2C6H5
B) C6H5CH2COOH
C) C6H5CH2Cl
D) C6H5CHClCOOH
E) O=C(CH2C6H5)2
Ans:
1312
Section: 17.3
43. Predict the major organic product of the reaction sequence below:
heat H3O+
+ KMnO4 ?
H2O, OH
OH
OH CO2H CHO
I II III
OH
CHO
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Section: 17.3
44. What is the expected product, A, of the following reaction sequence?

Cl i. NaCN A + NH4+
ii. 70% H2SO4, reflux
A) HCO2CH2C6H5
B) C6H5CH2COOH
C) C6H5CH2OSO3H
D) C6H5CHClCOOH
E) O=C(CH2C6H5)2
Ans:
1313
Section: 17.3
Cl
i. Mg/ether
ii. CO2 A
iii. H+
A) HCO2CH2C6H5
B) C6H5CH2COOH
C) C6H5CH2OSO3H
D) C6H5CHClCOOH
E) O=C(CH2C6H5)2
Ans:
Topic: Synthesis
Section: 17.3
46. Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?
A) i. Mg, Et2O
Br
ii. CO2
iii. H3O+
B) OH i. KMnO , OH, heat
4
ii. H3O+
C) i. CN
Br
ii. OH, H2O, heat
iii. H3O+
D) All of these
E) Answers A) and B) only
Ans:
1314
Topic: Synthesis
Section: 17.3
47. Which of the following would serve as syntheses of (CH3)3CCO2H?

A) O i. Cl2/OH(excess)
ii. H3O+
B) i. CN
Br
ii. H3O+ (heat)
C) i. Mg, Et2O
Br
ii. CO2
iii. H3O+
D) Answers A) and B) only
E) Answers A) and C) only
Ans:
Topic: Methods and Miscellaneous
Section: 17.3
48. 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+
Ans:
1315
Section: 17.3
49. 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+
Ans:
Section: 17.3
50. Reasoning by analogy, one would predict that the reaction of carbon disulfide with sec-
butylmagnesium bromide should yield which of the following (after acidification)?
S S
SH
SH SH
I II III
S
S
SH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1316
Section: 17.3

Cl i. NaCN A + NH4+
A) Benzyl formate
B) Phenylacetic acid
C) Benzenesulfonic acid
D) 1-chloro-1-phenyl acetic acid
E) Dibenzylketone
Ans:
Section: 17.3
52. What is the reactant of the following reaction sequence?

i. NaCN COOH
? + NH4+
A) BrCH2C6H5
B) C6H5CH2COOH
C) C6H5CH2OH
D) C6H5CH2CH2COOH
E) O=C(CH2C6H5)2
Ans:
1317
Section: 17.3
53. What would be the final product, F, of the following sequence of reactions?
i. LAH, Et2O PBr3 i. Mg, Et2O
CO2H ii. H O F
2 ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
Section: 17.3
CO2H ii. H O F
2 ii. CO2
iii. H3O+
A) 1-Bromo-2-methyl propane
B) 3-Bromo-3-methylbutanoic acid
C) Butanoic acid
D) 3-Methylbutanoic acid
E) Methyl 2-methylproanoate
Ans:
1318
Section: 17.3
2-methylpropanoic acid F
ii. H2O ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1319
Section: 17.3
56 What is the reactant of the following reaction sequence?

. ? i. LAH, Et2O PBr3 i. Mg, Et2O
CO2H
ii. H2O ii. CO2
iii. H3O+
Br CO2H CO2H
Br CO2H
O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1320
Section: 12.3 and 17.3
57. What would be the final organic product of the following reaction?
i. Mg, Et2O i. LAH, Et2O
Br ?
ii. CO2 ii. H2O
iii. H3O+
A) (CH3)3CCO2H
B) (CH3)3CCOCH3
C) (CH3)3CCH2OH
D) (CH3)3COCH3
E) (CH3)3CCO2CH3
Ans:
i. Mg, Et2O i. LAH, Et2O
Br ?
ii. CO2 ii. H2O
iii. H3O+
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
Ans:
1321
NaCN i. excess LAH, Et2O

C6H5 Cl ?
ii. H2O
A) C6H5CH2CH2CO2H
B) C6H5CH2CH2NH2
C) C6H5CH2CH(CH3)CN
D) C6H5CH2CH=NH
E) C6H5CH2NH2
Ans:

Section: 17.4
60. 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
Ans:
1322
Section: 17.4
61. 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
Ans:

Section: 17.4
62. Which compound would be most reactive toward nucleophilic acyl addition-
elimination?
A) CH3CO2Na
B) CH3COCl
C) (CH3CO)2O
D) CH3CONH2
E) CH3CO2CH3
Ans:
1323
Section: 17.4
63. 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
Ans:

Section: 17.4
64. 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
Ans:
1324
Section: 17.5
65. 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
Ans:
Topic: Synthesis
66. 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
Ans:
1325
Section: 17.7
67. What would be the product of the following reaction ?

18
OH O HA ?
+ H
O
18O O 18O
O 18O 18 O
I II III
18
O O O
O O
II III
\
A) I
B) II
C) III
D) IV
E) V
Ans:
1326
Section: 17.7
68. Predict the major organic product of the reaction sequence,

O O O i. CH3CH2OH
ii. dilute HCl, cold M
O O O
OCH2CH3 OH OCH2CH3O
HO HO H3CH2CO
O O O
I II III
H3CH2CO O OCH2CH3 H3CH2CO O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1327
Section: 17.7
69. The product of the following reaction is:

O
heat ?
O + OH
O
(1 mol) (1 mol)
O O O O
O O OH
CO2H CO2H
I II III
O O O
O H O
O
Cl O Cl
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1328
Section: 17.7
70. What is the product of this reaction?

O
CH3OH ?
O
O O
O CO2H HO O
O O
I II III
O O HO O
O
O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1329
Topic: Synthesis
Section: 17.7
71. 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
Ans:
Topic: Synthesis
Section: 17.7
72. 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) Answers A) and C) only
E) Answers A), B), and C)
Ans:
1330
Topic: Synthesis
Section: 17.7
73. Which of the following would serve as a reasonable synthesis of ethyl benzoate?
A) C6H5 OH HA
+ OH
O reflux
excess
B) C6H5 Cl
+ OH base
O
C) C6H5 O C6H5
+ OH
O O
D) All of the above
E) None of the above
Ans:
Topic: Synthesis
Section: 17.7
74. Which of the following combinations of reagents would not produce an ester?
A)
H3C ONa
+ Br
O
B) H3C ONa
+ OH
O
C) H3C OH
+ OH HA
O
D) H3C O CH3 OH
+
O O
E) H3C Cl
+ OH
O
Ans:
1331
Section: 17.7
75. 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
Ans:
Section: 17.7
76. - 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
Ans:
1332
Topic: Synthesis
Section: 17.7
77. Which of the following would yield (S)-2-butanol?

A) i. CH3CO2Na+
(R)-2-Bromobutane 
ii. OH , H2O, heat

B) OH , H2O, heat
(R)-2-Bromobutane
C) (S)-sec-Butyl acetate OH, H2O, heat
D) All of these
E) None of these
Ans:
Section: 17.7
78. What final product, Q, would be obtained via the following reaction sequence?
O
H3C H C6H5 Cl OH/ H2O O
Q +
H OH pyridine heat C6H5 O
A) cis-3-Methylcyclopentanol
B) trans-3-Methylcyclopentanol
C) Equal amounts of A) and B)
D) 3-Methylcyclopentanone
E) None of these
Ans:
1333
Section: 17.7
79. (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 A) and B)
D) 2-Hexene (cis and trans)
E) 1-Hexen-2-ol
Ans:
Section: 17.7
80. 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) (R,S)-2-methyl-3-pentanol
D) 2-Methyl-2-pentene
E) (R,S)-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts
Ans:
1334
Topic: Synthesis
Section: 17.7
81. 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) Answers A) and C) only
E) Answers A), B), and C)
Ans:
1335
O
O 1. LAH
?
2. H3O+
O HO
OH OH
I III
II
OH
O
HO OH
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
1336
O
O
i. DIBAL-H, -78oC ?
ii. H3O+
O HO
OH OH
I III
II
OH
O
HO OH
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
1337
O
i. DIBAL-H, -78oC ?
O
ii. H3O+
O
OH HO OH
I III
II
OH
O HO OH
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
1338
O
i. DIBAL-H, -78oC ?
O
ii. H3O+
O
OH
OH
OH
O
OH
I III
O II OH
O O
V
O
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
1339
Topic: Synthesis
CH3CH2CH2CO2CH3  CH3CH2CH2CHO

A) H2/Ni
B) Li/liq NH3
C) Al(CH2CH(CH3)2)2H
D) NaBH4, CH3OH
E) LiAlH4, ether
Ans:
1340
87. The product, Z, of the following sequence of reactions is which compound?

i. KMnO4, OH, heat
ii. H3O+
p-Chlorotoluene Z
iii. SOCl2
iv. CH3CH2OH, base
O O
O O
Cl Cl
I II III
O O
Cl
Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1341
88. 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+
Ans:
1342
89. Predict the major organic product, P, of the following sequence of reactions:
Cl i. OH (2eq.), H2O heat H2 i. SOCl2

P
CO2H +
ii. H3O cat. ii. CH3OH
Cl
O O
O
CO2H O
O
I II III
Cl
O O
O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1343
Topic: Synthesis
90. Which of the following reactions would constitute a reasonable synthesis of propyl
acetate?
A) OH HA
OH +
O
B) Cl pyridine
OH +
O
C) O
OH +
O O
D) All of these
E) None of these
Ans:
Section: 17.8
91. What is the product of this reaction?

O
H2 O
HN ?
OH-
O O
H H2N O
N CO2H O N
H
I II III
O O HO O
HN
O N
H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1344
Section: 17.8
92. 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
Ans:
Section: 17.8

O O O i. NH3, H2O
M
ii. dilute HCl, cold
O O O
OH NH2 NH2
HO HO H2N
O O O
I II III
H
O N O HN O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1345
Section: 17.8

O
i. NH3, H2O
O ?
ii. dilute H+, cold
O
O O O
OH NH2 NH2
OH OH NH2
O II O III O
I
O NH
NH O
O V O
IV
A) I
B) II
C) III
D) IV
E) V
Ans:
1346
Section: 17.8

O O O i. NH3, H2O
M
ii. dilute HCl, cold
O O
OH NH2
O
NH2 NH2
NH2
HO
O O O
I II III
H
O N O HN O O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1347
Topic: Synthesis
Section: 17.8
96. N,N-Dimethylbenzamide can be made from which of the following?

A) C6H5 O + N
H
O
B) C6H5 Cl
+ N
O H
C) C6H5 O C6H5
+ N
O O H
D) C6H5 NH2
+ CH3MgCl
O
E) A), B), and C) only
Ans:
Section: 17.8
97. What would be the final product?
P4O10 i. CH3MgI, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
A) C6H5CH2CO2CH3
B) C6H5CH2CH2NHCH3
C) C6H5CH2COCH3
D) C6H5CH2CH(CH3)CN
E) C6H5CH2CH=NCH3
Ans:
1348
Section: 17.8
P4O10 i. CH3Li, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
A) C6H5CH2CO2CH3
B) C6H5CH2CH2NHCH3
C) C6H5CH2COCH3
D) C6H5CH2CH(CH3)CN
E) C6H5CH2CH=NCH3
Ans:
Section: 17.8
P4O10 i. DIBAL-H, -78oC

C6H5CH2CONH2 ?
heat ii. H3O+
A) C6H5CH2CO2CH3
B) C6H5CH2CH2NHCH3
C) C6H5CH2COCH3
D) C6H5CH2CH(CH3)CN
E) C6H5CH2CHO
Ans:
1349
Section: 17.8
P4O10 i. PhLi, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
A) C6H5CH2CO2Ph
B) C6H5CH2CH2NHPh
C) C6H5CH2COPh
D) C6H5CH2CH(Ph)CN
E) C6H5CH2CH=NPh
Ans:
Section: 16.5B and 17.8
101. 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.
Ans:
1350

i. PCl5
CO2H ?
ii. NH3
iii. P4H10, heat
A) CH3CH2CH2NH2
B) CH3CH2CONH2
C) CH3CH2CONHCOCH2CH3
D) CH3CH2CN
E) CH3CH2COO-NH4+
Ans:
103. What would be the final product of this reaction sequence?

CO2H i. PCl3
?
ii. NH3
iii. P4O10
O
CN NH2 NH2
I II III
H H
CO2 NH4 N N
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1351
Section: 16.5B, 17.5, and 17.8

i. PCl5
CO2H ?
ii. NH3
iii. P4H10, heat
iv. CH3MgBr, ether
A) CH3CH2CH2NH2
B) CH3CH2CONH2
C) CH3CH2CONHCOCH2CH3
D) CH3CH2CN
E) CH3CH2COCH3
Ans:
Section: 16.5B, 17.5 and 17.8
105. What would be the final product of this reaction sequence?

i. PCl3
CO2H ii. NH3
?
iii. P4O10
iv. CH3Li, ether
v. H3O+
O
CN NH2 NH2
I II III
H H
COCH3 N N
O
IV V
A) I
B) II
C) III
D) IV
E) V
1352
Ans:
1353
Section: 17.3, 17.5 and 17.8
106. What is the final product of this sequence of reactions?

i. Mg, Et2O i. SOCl2
Br ?
ii. CO2 ii. excess NH3
iii. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1354
Section: 17.3, 17.5 and 17.8
107. What is the final product of this sequence of reactions?

i. Mg, Et2O i. SOCl2 P4O10
Br ?
ii. CO2 ii. excess NH3 heat
iii. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1355
Section: 17.9
108. What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5NC=O?
A) H
N O
C6H5
O
B) CO2H
N
C6H5
C) CHO
N
C6H5 O
D) H
N O
C6H5
O
E) H
N
C6H5
O
Ans:
1356
Section: 17.9
109. What is the ultimate product of this sequence of reactions?

O
CH3CH2OH CH3NH2
Cl Cl ?
(1 eq.)
O O O
H H O Cl
N N Cl N
O N O O
H O
H O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1357
Topic: Nomenclature
Section: 17.9
110. Which of the following structures is 3,4-dimethylpentyl chloroformate?

H O Cl O Cl O
O O O
Cl
I II III
O Cl O
O Cl O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1358
Section: 17.10
111. Identify the product(s) of the following reaction.

O
heat
CO2H ?
O O
O O + CO2
OH O
I II III
CO2H
+ CO 2 CO2H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1359
Section: 17.10

O H3O+
CO2CH3 ?
heat
O O
O O + CO2 + CH3OH
OH O
I II III
CO2H
+ CO 2 CO2H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1360
Section: 17.10

O
COOH
heat
?
OH O
COOH COOH
I II III
COOH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans:
1361
Topic: Synthesis
Section: 17.10
114. Which carboxylic acid would decarboxylate when heated to 100-150C?

CO2H O
HO2C HO2C CO2H
CO2H
I II III
A) I
B) II
C) III
D) More than one of these
E) None of these
Ans:
Topic: Synthesis
Section: 17.10
115. 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
Ans:
1362
116. 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
E) None of these
Ans:

117. 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
Ans:
1363
118. 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
Ans:
Topic: Synthesis
Sections: 12.3 and 17.13
CH3CH2CH2COOH  CH3CH2CH2CH2OH

A) H2/Ni
B) Li/liq NH3
C) LiAlH[OC(CH3)3]3
D) NaBH4, CH3OH
E) LiAlH4, ether
Ans:
Topic: Synthesis
Sections: 12.3 and 17.13
CH3C≡CCH2CO2CH2CH3  CH3C≡CCH2CH2OH

A) H2/Ni
B) Li/liq NH3
C) LiAlH[OC(CH3)3]3
D) NaBH4, CH3OH
E) LiAlH4, ether
Ans:
1364
Topic: Synthesis
Sections: 15.7 – 15.9, and 17.13
121. Which of the reactions listed below would serve as a synthesis of acetophenone,
C6H5COCH3 ?
A)
AlCl3
(CH3CO)2O + C 6H 6
B) O AlCl3
+ C6H6
H3C Cl
C) O
+ CH3MgI
C6H5 OCH3
D) Two of these
E) All of these
Ans:
Sections: 16.4C and 17.13
i. LiAl(OC(CH3)3)3H,-78oC
C6H5COCl ?
+
ii. H3O
A) C6H5CO2H
B) C6H5CH3
C) C6H5COOCH3
D) C6H5CHO
E) C6H5CH2OH
Ans:
1365
Sections: 16.4C , 16.7 and 17.13
i. LiAl(OC(CH3)3)3H HO OH
C6H5COCl ?
+ +
ii. H3O H
A)
O O
C6H5CH
B) C6H5CH3
C) C6H5COOCH2CH2OH
D) C6H5CHO
E) C6H5CH2OH
Ans:
Sections: 16.4C , 16.8 and 17.13
i. LiAl(OC(CH3)3)3H CH3NH2
C6H5COCl ?
+
ii. H3O pH 4-5
A) C6H5CO2H
B) C6H5CH2CH2NCH3
C) C6H5CH2CH2CN
D) C6H5CH=NCH3
E) C6H5CH2NCH3
Ans:
1366
SHORT ANSWER QUESTIONS
Topic: Nomenclature
Section: 17.2
125. While the IUPAC name for HCO2H is methanoic acid, it is commonly known as
__________.
Ans:
Topic: Nomenclature
Section: 17.2
126. Ethanoic acid (CH3CO2H) is usually called _______________, from the Latin for
“vinegar”.
Ans:
Topic: Nomenclature
Section: 17.2
127. Draw the structure for 3-methylbutanoic anhydride.

Ans:
Topic: Nomenclature
Section: 17.2
128. Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile.

Ans:
Topic: Nomenclature
Section: 17.2
129. Draw the structure for 3-oxo-5-bromohexanoic acid.

Ans:
1367
1368
Topic: Nomenclature
Section: 17.2
130. Draw the structure for 4-methylpentyl 3-ethylpentanoate.

Ans:
Section: 17.2
131. Suggest a structure consistent with the following spectroscopic data:

C5H10O2
IR: 1745cm−1
1
H NMR:
triplet 3H,  0.90
multiplet 2H,  1.60
singlet 3H,  1.95
triplet 2H,  3.95
13
C NMR
Broadband decoupled: 10.41, 20.91, 22.14, 66.10, 171.09 
DEPT 90: no peaks
DEPT 135: 10.41, 20.91  (positive); 22.14, 66.10  (negative)
Ans:
1369
Section: 17.2
132. A compound has the formula C7H14O2. The 13C and 1H NMR spectral data for this
compound are:
13
C 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
1
H 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.

Ans:
Section: 17.2
133. A compound has the formula C6H11BrO2. The 13C and 1H NMR spectral data for this
compound are:
13
C 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
1
H NMR
2.18 δ, multiplet (2H)
4.15 δ, quartet (2H)
Suggest a structure consistent with this data.
Ans:
1370
Topic: Miscellaneous
Section: 17.2C
134. The presence of electron-withdrawing substituents close to the carboxylic acid

functional group will ___________ the acidity of the molecule by _________.
Ans:
Section: 17.2F
135. The only carboxylic acid derivative with two carbonyl groups is the ___________.
Ans:
Section: 17.2H
136. The linkages that join amino acids together to form proteins are primarily ___________
bonds.
Ans:
Topic: Reaction Sequence and Mechanistic Pathways

Section: 17.3
137. 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?
Br
OH
Ans:
1371
Section: 17.3

with
OH
Br
O
HO
HO
Ans:

Section: 17.3

with
Cl
OH
Ans:

Section: 17.3

with
1372
OH
Cl
O
Ans:

Section: 17.3

with
OH
Br
Ans:
Topic: Reaction Mechanisms
Section: 17.4
142. Acyl compounds tend to react by acyl substitution mechanisms because they all have a
good or reasonably good ________________ attached to the carbonyl carbon.
Ans:
1373
Section: 17.7
143. Cyclic esters are called _____________, while cyclic amides are called _________.
Ans:
Section: 17.7
144. An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol) is

called a ________________.
Ans:
Section: 17.7
145. Base-promoted hydrolysis of esters is sometimes called ______________.

Ans:
Topic: Reactions
Section: 17.7
146. When a gamma-hydroxy acid is treated with dilute acid, cyclization occurs, producing a
______________.
Ans:
Topic: Reaction Sequence
147. Complete the following reaction sequence, giving details of all significant intermediates.
O
i.) 2 equiv CH3Li
ii.) CH3I ?
O
Ans:
1374
1375
148. Suggest a suitable synthetic strategy for the transformation of 3-methyl-1-pentanol into
propyl 3-methylpentanoate
Ans:
Section: 12.3, 17.3 and 17.7
i. KMnO4, OH-, H2O
ii. H3O+
?
iii. NaBH4, H2O
iv. H3O+
Ans:
1376
Section: 17.5 and 17.8B
O i.) SOCl2
?
OH ii.) CH3CH2CH2NHCH3
Ans:
Section: 17.8I
151. The functional group in a lactam is _________________.

Ans:
Section: 17.9
OH
i. COCl2 (1 equivalent) ?
ii. CH3CH2CH2CH2NHCH3
Ans:
Section: 17.11
153. Litmus paper turns ___________ when an aqueous solution of a carboxylic acid is
dropped on it.
Ans:
1377
Topic: Physical Properties, Isolation
154. Given a mixture of benzylalcohol, phenol, and benzoic acid dissolved in ether,
outline
in a flow diagram an extraction method to separate each.
Ans:
1378

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Chapter Seventeen

MULTIPLE CHOICE QUESTIONS

1. Which compound would be the strongest acid?

2. Which compound would be the weakest acid?

3. The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm -1 and

5. The correct structure for ethyl 3-methylbutanoate is:

7. The correct structure for ethyl 2-methylbutyl 3-methylbutanoate is:

What is the IUPAC name for O

9. The correct structure for ethyl 2-chloropenanoyl chloride is:

11. The correct structure for ethyl dimethylbutyl methanoate is:

12. Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

17. Which of the following would be the strongest acid?

18. Which of the following would be the weakest acid?

19. Which of the following would be the strongest acid?

20. Which of the following would be the strongest acid?

21. Which of the following would be the strongest acid?

O2N O2N NO2

NO2 O2N NO2

22. Which of the following would be the strongest acid?

H3C H3C CH3

CH3 H3C CH3

23. Which of the following would be the strongest acid?

H3CO H3CO OCH3

OCH3 H3CO OCH3

24. Which of the following would be the weakest acid?

H3CO H3CO OCH3

OCH3 H3CO OCH3

25. Which of the following would be the weakest acid?

H3C H3C CH3

CH3 H3C CH3

29. Which compound would be most acidic?

The most likely structure for the compound is:

37. Which of the following would be the strongest acid?

38. Which of the following would be the weakest acid?

39. Which of the following would be the strongest acid?

40. Which compound would be most acidic?

42. What is the reactant of the following reaction sequence?

44. What is the expected product, A, of the following reaction sequence?

46. Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?

47. Which of the following would serve as syntheses of (CH3)3CCO2H?

48. Which of these combinations will not produce benzoic acid?

49. Which of these combinations will not produce benzoic acid?

51. What is the expected product, A, of the following reaction sequence?

52. What is the reactant of the following reaction sequence?

56 What is the reactant of the following reaction sequence?

NaCN i. excess LAH, Et2O

Topic: Chemical Tests, Relative Reactivities, and Physical Properties

61. Which of these compounds could not be formed by nucleophilic attack by an

Topic: Chemical Tests, Relative Reactivities, and Physical Properties

Topic: Chemical Tests, Relative Reactivities, and Physical Properties

CH3CH2CH2COCl  CH3CH2CH2CHO

67. What would be the product of the following reaction ?

68. Predict the major organic product of the reaction sequence,

H3CH2CO O OCH2CH3 H3CH2CO O O

69. The product of the following reaction is:

70. What is the product of this reaction?

71. Which of the following compounds is capable of forming a -lactone?

A) CH3CH2OH + (CH3CO)2O + pyridine 

77. Which of the following would yield (S)-2-butanol?

C) (S)-sec-Butyl acetate OH, H2O, heat

79. (R)-3-hexanol is subjected to the following sequence of reactions: i) acetyl chloride,

80. Predict the final product likely to be obtained when (S)-2-methyl-3-pentanol is

A) Benzyl alcohol + acetic anhydride 