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CHEMISTRY 2218-Spring 2011 CH17 (HW-5)
1. Which of the following is the best name for the following compound?
O
O
A) Isobutyl ethanoate B) Ethyl isopropanoate C) 3-methylbutyl ethanoate D) Ethoxy isobutyl ketone E) Ethyl 3-methylbutanoate Ans: E
2.
A correct name for O
O
is: A) 2-Methylbutyl 2-methylbutanoate B) 2-Methylbutyl 3-methylbutanoate C) 3-Methylbutyl isovalerate D) Isopentyl isovalerate E) Isopentyl isobutyrate Ans: B
3. Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?
N
O
III
HN
O
I
N
O
II
N
O
IV V
N
O
A) I B) II C) III D) IV E) V Ans: E
4. 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 Ans: B
5. Which of the following would be the strongest acid?
IIII II
Cl
CO2H
IV VCl
CO2H
Cl
CO2H CO2H
Cl Cl
CO2HCl
Cl
A) I B) II C) III D) IV E) V Ans: C
6. A compound has the molecular formula C8H14O4. Its IR spectrum shows a strong absorption band near 1740 cm-1. Its 1H NMR spectrum consists of: triplet, δ 1.3 singlet, δ 2.6 quartet, δ 4.2 The most likely structure for the compound is:
IV V
O
OO
O O
O
O
OO
OO
OI II III
HO2C CO2H O OO
O
A) I B) II C) III D) IV E) V Ans: A
7. What is the reactant of the following reaction sequence?
i. Mg/etherii. CO2iii. H+
OH
O
?
A) HCO2CH2C6H5 B) C6H5CH2COOH C) C6H5CH2Cl D) C6H5CHClCOOH E) O=C(CH2C6H5)2 Ans: C
8. Which of the following would serve as syntheses of (CH3)3CCO2H? A) i. Cl2/OH− (excess)
ii. H3O+
O
B) Br
i. CN−
ii. H3O+ (heat)C)
Bri. Mg, Et2O
ii. CO2
iii. H3O+
D) Answers A) and B) only E) Answers A) and C) only Ans: E
9. What would be the product of the following reaction ? OH
O
OH
O
O
O
O
O
O
O
O
O O
O
I II III
II III
HA+ ?18
18 18
18
18 18
\ A) I B) II C) III D) IV E) V Ans: A
10. Which of the following would serve as a reasonable synthesis of ethyl benzoate? A)
O
OHC6H5 OH+ HA reflux
excessB)
O
ClC6H5 OH+ base
C) O
OC6H5 C6H5
OOH+
D) All of the above E) None of the above Ans: D
11. What would be the final organic product of the following reaction?
i. DIBAL-H, -78oCii. H3O+
?
OH HO OH
OHHO
III
III
IV
V
O
O
O
O
OH
A) I B) II C) III D) IV E) V Ans: D
12. 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: C
13. What is the product of this reaction?
HN
O
CO2HHN H2N O
O
IIII II
O NH
O
O
O
NH
O
IV V
HNOHO
?H2O
OH-
A) I B) II C) III D) IV E) V Ans: B
14. Predict the major organic product of the reaction sequence, OO O
HO
OOH
OHO
ONH2
OH2N
ONH2
O
OHN O
I II III
IV V
HNO O
Mi. NH3, H2O ii. dilute HCl, cold
A) I B) II C) III D) IV E) V Ans: B
15. Predict the major organic product of the reaction sequence, OO O
HO
ONH2
O
OHN O
I II III
IV V
HNO O
Mi. NH3, H2O ii. dilute HCl, cold
OH
O
NH2
O
NH2
O
NH2
O
A) I B) II C) III D) IV E) V Ans: A
16. What would be the final product?
C6H5CH2CONH2i. CH3Li, Et2Oii. H3O+
P4O10heat ?
A) C6H5CH2CO2CH3 B) C6H5CH2CH2NHCH3 C) C6H5CH2COCH3 D) C6H5CH2CH(CH3)CN E) C6H5CH2CH=NCH3 Ans: C
17. What would be the final product?
C6H5CH2CONH2i. PhLi, Et2Oii. H3O+
P4O10heat ?
A) C6H5CH2CO2Ph B) C6H5CH2CH2NHPh C) C6H5CH2COPh D) C6H5CH2CH(Ph)CN E) C6H5CH2CH=NPh Ans: C
18. What would be the final product of this reaction sequence?
I II III
V
CN NH2
O
HN
HN
O
NH2
CO2H
IV
CO2 NH4
i. PCl3ii. NH3iii. P4O10
?
A) I B) II C) III D) IV E) V Ans: A
19. What is the final product of this sequence of reactions?
I II III
IV V
Br
O
ONH2 CN
NH2NHCl
O
NH2
O
i. SOCl2ii. excess NH3
?i. Mg, Et2O
ii. CO2
iii. H3O+
A) I B) II C) III D) IV E) V Ans: C
20. What is the final product of this sequence of reactions?
I II III
IV V
Br
O
ONH2 CN
NH2NHCl
O
NH2
O
i. SOCl2ii. excess NH3
?i. Mg, Et2Oii. CO2iii. H3O+
P4O10
heat
A) I B) II C) III D) IV E) V Ans: B
21. What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5N=C=O?A)
C6H5
HN O
OB)
C6H5NCO2H
C)
C6H5N
O
CHO
D)
C6H5
HN O
O E)
C6H5
HN
O Ans: A
22. Which of the following structures is 3,4-dimethylpentyl chloroformate?
H O
O Cl
I
Cl O
O
II
Cl O
O
III
O
O Cl
IV
Cl O
O
VA) I B) II C) III D) IV E) V Ans: E
23. Identify the product(s) of the following reaction. O
CO2H
O
O
OH O
CO2H
I II III
IV V
O
O
CO2H
heat?
+ CO2
+ CO 2
A) I B) II C) III D) IV E) V Ans: C
24. Which carboxylic acid would decarboxylate when heated to 100-150°C?
HO2CCO2H
I
CO2HO
II
HO2C CO2H
IIIA) I B) II C) III D) More than one of these E) None of these Ans: D
25. 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: D
26. 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: D
27. Which of the reactions listed below would serve as a synthesis of acetophenone, C6H5COCH3 ? A)
(CH3CO)2O + C6H6
AlCl3
B) H3C Cl
O AlCl3+ C6H6
C) C6H5 OCH3
O+ CH3MgI
D) Two of these E) All of these Ans: D
28. What would be the final organic product of the following reaction?
C6H5COCli. LiAl(OC(CH3)3)3H
ii. H3O+?
pH 4-5
CH3NH2
A) C6H5CO2H B) C6H5CH2CH2NCH3 C) C6H5CH2CH2CN D) C6H5CH=NCH3 E) C6H5CH2NCH3 Ans: D
29. 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: D
30. 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: D
31. What is the final product of this sequence of reactions?
I II III
IV V
Br
O
ONH2 CN
NH2NHCl
O
NH2
O
i. SOCl2ii. excess NH3
?i. Mg, Et2Oii. CO2iii. H3O+
P4O10
heat
A) I B) II C) III D) IV E) V Ans: B
32. What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5N=C=O?A)
C6H5
HN O
OB)
C6H5NCO2H
C)
C6H5N
O
CHO
D)
C6H5
HN O
O E)
C6H5
HN
O Ans: A
33. What is the ultimate product of this sequence of reactions?
Cl NH
O
IV
O Cl
O
HN
HN
OO N
H
O
Cl Cl
O
I II III
O O
O
V
CH3NH2CH3CH2OH (1 eq.)
?
A) I B) II C) III D) IV E) V Ans: A
34. What would be the final product?
C6H5CH2CONH2i. CH3Li, Et2Oii. H3O+
P4O10heat ?
A) C6H5CH2CO2CH3 B) C6H5CH2CH2NHCH3 C) C6H5CH2COCH3 D) C6H5CH2CH(CH3)CN E) C6H5CH2CH=NCH3 Ans: C
35. What would be the final product?
C6H5CH2CONH2i. DIBAL-H, -78oCii. H3O+
P4O10heat ?
A) C6H5CH2CO2CH3 B) C6H5CH2CH2NHCH3 C) C6H5CH2COCH3 D) C6H5CH2CH(CH3)CN E) C6H5CH2CHO Ans: E
36. Predict the major organic product of the reaction sequence,
O
O
O
i. NH3, H2O
ii. dilute H+, cold?
OH
OH
O
O
NH2
OH
O
O
NH2
NH2
O
O
NH
O
O
O
NH
O
I II III
IV V
A) I B) II C) III D) IV E) V Ans: B
37. Predict the major organic product of the reaction sequence, OO O
HO
ONH2
O
OHN O
I II III
IV V
HNO O
Mi. NH3, H2O ii. dilute HCl, cold
OH
O
NH2
O
NH2
O
NH2
O
A) I B) II C) III D) IV E) V Ans: A
38. Which of the following reactions would constitute a reasonable synthesis of propyl acetate? A)
OHOH
O
HA+
B) OH
Cl
O+
pyridine
C) OH
O
O+
OD) All of these E) None of these Ans: D
39. What is the product of this reaction?
HN
O
CO2HHN H2N O
O
IIII II
O NH
O
O
O
NH
O
IV V
HNOHO
?H2O
OH-
A) I B) II C) III D) IV E) V Ans: B
40. 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: C
