FINAL EXAM
Covering all chapters, including 12, 13, 15, 16, 17, 18, 19, 20, 21, and 22
Name_________________________________________
Instructions – Answer ALL 50 of the 50 questions for a grade. Students
MUST SHOW work per question – either provide a statement where
necessary and/or show the mechanism to arriving the correct answer – to
receive full credit for the entire test. If work is not shown, even if it is one
question missing, students WILL NOT receive credit for the entire test.
Answers are to be recorded in BlackBoard for immediate score.
Multiple Choice and True/False (T = A, F = B)
Multiple Choice
1. What is the major organic product obtained from the following intramolecular aldol condensation reaction?
a.
b.
c.
d.
1
2
3
4
2. What is the major organic product obtained from the following intramolecular Claisen Condensation
(Dieckmann) reaction?
1
a.
b.
c.
d.
1
2
3
4
3. What is the major organic product obtained from the following Claisen Condensation reaction, starting with
two moles of ester?
2 mols
2
a.
b.
c.
d.
1
2
3
4
4. What is the major organic product obtained from the following sequence of reactions?
a.
b.
c.
d.
1
2
3
4
5. What is the major organic product obtained from the following reaction?
3
a.
b.
c.
d.
1
2
3
4
6. What is the major organic product obtained from the following aldol condensation reaction?
2 mols
a.
b.
c.
d.
1
2
3
4
7. What is the major organic product obtained from the following Cross Aldol Condensation reaction?
a.
b.
c.
d.
1
2
3
4
4
8. What is the major organic product obtained from the following Cross Claisen condensation reaction?
a. 1
b. 2
c. 3
d. 4
9. What is the major organic product obtained from the following 1,2 addition reaction?
a. 1
b. 2
c. 3
d. 4
10. What is the major organic product obtained from the following Robinson Annulation reaction?
a. 1
5
b. 2
c. 3
d. 4
11. What is the major organic product obtained from the following sequence of reactions? Reaction steps include
alkylation, saponification, acidification, followed by thermal decarboxylation.
a.
b.
c.
d.
1
2
3
4
12. What is the major organic product obtained from the following sequence of reactions? Reaction steps include
alkylation, saponification, acidification, thermal decarboxylation, followed by esterification.
a.
b.
c.
d.
1
2
3
4
6
13. What is the major organic product obtained from the following 1,4 addition reaction?
a.
b.
c.
d.
1
2
3
4
14. What is the major organic product of the following sequence of reactions?
a.
b.
c.
d.
1
2
3
4
15. What is the major organic product of the following sequence of reactions?
7
a.
b.
c.
d.
1
2
3
4
16. What is the major organic product of the following sequence of reactions?
a. 1
b. 2
c. 3
d. 4
17. What is the major organic product of the following sequence of reactions?
a. 1
b. 2
8
c. 3
d. 4
18. What is the major organic product of the following sequence of reactions?
a. 1
b. 2
c. 3
d. 4
19. Which of the following compounds gives an infrared spectrum with peaks at 3300 cm1 (sharp peak) and
2150 cm1 (sharp peak)?
a.
b.
c.
d.
1
2
3
4
20. Which of the following compounds gives a carbonyl bond absorption at the highest frequency?
a.
b.
c.
d.
1
2
3
4
21. What is the major organic product obtained from the following sequence of reactions?
9
a.
b.
c.
d.
1
2
3
4
22. What is the major organic product obtained from the following sequence of reactions?
a.
b.
c.
d.
1
2
3
4
23. Which of the following is the reactive intermediate formed in the electrophilic nitration of nitrobenzene with
HNO3 and H2SO4?
10
a.
b.
c.
d.
1
2
3
4
11
24. Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion?
a.
b.
c.
d.
1
2
3
4
25. Which C9H10O compound gives the following 1H NMR spectrum?
12
a.
b.
c.
d.
1
2
3
4
26. What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of 1-bromo-2methylpropane?
a. singlet
b. doublet
c. triplet
d. Nonet
27. Which C6H12O2 compound gives the following 1H NMR spectrum?
a. 1
b. 2
c. 3
13
d. 4
28. Which of the following sets of molecular ions does an alkyl bromide possess?
a. two molecular ions in a 2:1 ratio separated by two mass units
b. two molecular ions in a 1:1 ratio separated by two mass units
c. three molecular ions in a 1:2:1 ratio separated by two mass units
d. two molecular ions in a 3:1 ratio separated by two mass units
29. Which of the following energy diagrams represents the electronic state of butadiene after absorption of
radiation?
a. 1
b. 2
c. 3
d. 4
30. What is the major organic product obtained from the following sequence of reactions?
a. 1
14
b. 2
c. 3
d. 4
31. What is the major organic product obtained from the following sequence of reactions?
a. 1
b. 2
c. 3
d. 4
True or False: a – True, b – False
32. Consider the following reactants. This is an example of a Suzuki reaction. T or F
MATCH a structure from the list below to the following IR spectra. Place the letter of the structure in the blank
provided.
33. The spectrum below belongs to letter F. T or F
15
34. The spectrum below belongs to letter D. T or F
35. The spectrum below belongs to letter C. T or F
16
36. The NMR spectrum below is that of butanal. T or F
37. The NMR spectrum below is that of 3-phenylpropanoic acid, PhCH2CH2CO2H. T or F
For questions 38 and 39, confirm (or not) the number of carbon atoms that should be in their 13C
NMR spectra.
17
38. The compound has five different carbon atom signals. Tor F
39. The compound has five different carbon atom signals. T or F
40. The mass spectrum below shows evidence of chlorine in the compound. T or F
Refer to the mass spectrum of 2-methylbutane shown below to answer questions 41 - 44.
18
41. The peak at a m/z of __57___ represents M+. T or F
42. The peak at a m/z of __41___ represents the base peak. T or F
43. The peak at a m/z of __57___ represents the following species. T or F
44. The peak at a m/z of ___29__ represents the following species. T or F
45. Consider the following reaction.
The mechanism for this reaction is shown below. T or F
46. Consider the following reaction.
19
The reactant is a lactam. T or F
47. The predominant product from sequential nitration and bromination of benzenesulfonic acid is
shown below. T or F
48. The product of the following reaction would be classified as a carboxylic acid. T or F
49. The following spectrum could arise from  to * transitions. T or F
50. Furan has the structure shown below.
The  orbitals in furan are shown below. T or F
20