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. 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: B
3. 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: 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?
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: 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:

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: A
7. 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: C

8. 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: E
 9. 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: A

10. 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: D
11. What would be the final organic product of the following reaction?
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: 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?
O
H2O
HN ?
-
OH
O O
H O
N CO2H H2N
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: B

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

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: B
15. Predict the major organic product of the reaction sequence,
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: A

16. What would be the final product?

P4O10 i. CH3Li, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+

A) C6H5CH2CO2CH3
B) C6H5CH2CH2NHCH3
C) C6H5CH2COCH3
D) C6H5CH2CH(CH3)CN
E) C6H5CH2CH=NCH3
Ans: C
17. What would be the final product?

P4O10 i. PhLi, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+

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?

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: A
19. 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: C

20. 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: B
21. 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: A

22. 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: E
23. 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: C

24. 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: 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)
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: D

28. What would be the final organic product of the following reaction?

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: 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 Æ 2-methylpropanoic acid
B) 2-Ethylpropanedioic acid Æ Butanoic acid
C) 2-Methyl-3-oxo-pentanoic acid Æ 3-Pentanone
D) 2-Methyl-4-oxo-pentanoic acid Æ 2-Methyl-3-butanone
E) 4-Methyl-3-oxo-heptanoic acid Æ 3-Methyl-2-hexanone
Ans: D
31. 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: B

32. 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: A
33. 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 O
H H
O
I II III IV V

A) I
B) II
C) III
D) IV
E) V
Ans: A

34. What would be the final product?

P4O10 i. CH3Li, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+

A) C6H5CH2CO2CH3
B) C6H5CH2CH2NHCH3
C) C6H5CH2COCH3
D) C6H5CH2CH(CH3)CN
E) C6H5CH2CH=NCH3
Ans: C
35. What would be the final product?

P4O10 i. DIBAL-H, -78oC

C6H5CH2CONH2 ?
heat ii. H3O+

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

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: B
37. Predict the major organic product of the reaction sequence,
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: A

38. 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: D
39. What is the product of this reaction?
O
H2O
HN ?
-
OH
O O
H O
N CO2H H2N
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: 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