Problem Set 10
Chapters 12 and 14
Due: Monday, December 6, 2004
Material in this Problem Set will be covered in the final exam.
1. (30 pts) Treatment of compound A with catalytic HgSO4/aq. H2SO4 gives two constitutional isomers B and C. Exposure of B and C independently to NaBH4 affords compounds D and E, respectively. Hydrogenation of A provides n-octane.
a) What are the structures A-E?
b)What is the molecular ion for D and E and is it visible in the spectra?
[For larger versions of the spectra, click here.]
Compound D Compound E
2. (10 pts) (S)-Epichlorohydrin is treated successively with methyl magnesium bromide and isopropyl magnesium bromide to form chiral compound A. What is the structure of A and its absolute configuration? Explain and illustrate with a mechanism.
3. Thedata to the right represent the fragmentation patterns of two acyclic alkanes. What are their structures? Explain and illustrate? How many compounds are eligible for consideration? Which one is eliminated? Estimate the intensity of M+1=73.
c
Alkane 1
m/z
intensity
15
2
26
3
27
43
28
5
29
60
30
1
37
1
38
3
39
30
40
5
41
88
42
95
43
100
44
6
50
2
51
2
53
3
55
10
56
40
57
94
58
5
71
4
72
16
c
Alkane 2
m/z
intensity
26
1
27
22
28
3
29
20
38
1
39
12
40
2
41
50
42
78
43
100
44
4
53
1
55
4
56
3
57
20
72
17
4. (40 pts) Provide the missing information in each of the following reactions. Provide explanations and mechanisms. For 4d, see pg. 621.
5. (50 pts) Provide the structures of A-Z. Show your reasoning where it is called for. Be brief.