QUIZ #1/ Chem 227/ 2010

The Quiz MUST be done independently.

CONSIDER CAREFULLY:
You may consult printed and/or on-line references, with the following EXCEPTIONS: Do not e-mail "Ask Dr. Structure", do not use any previous Chem 227 students' work, and do not consult with any living, breathing organism; nor communicate with them in any way. The slightest evidence of infraction or colusion will result in a zero for all parties involved. This policy is non-negotiable.

1) Find your DVC ID number in the first column of the following table. Record the four assigned problem numbers for Easy, Medium, Medium, and Hard on the answer form that was handed out. (Only answers on the form will be accepted. There is also an on-line link to the form [pdf] if you need to print another.) The grading percentages for the degree of difficulty are weighted and scaled: 35 possible percentage points = easy; 25 points = medium; 15 points = hard.

2) Consult the link below for spectroscopic data. Provide structures for each of the problems on the form with accompanying justification (peak assignments) as done in previous lab Worksheets/Exercises.

http://www.nd.edu/~smithgrp/structure/workbook.html
Click on: Do The Problems

3) After solving the four problems provide a structure for "UNX", an unknown structure. The spectroscopic and weight percent data for UNX follows the assignment table. Assign all pertinent spectroscopic data to the structure as done previously in the lab Worksheets/Exercises.

Easy
Med
Med
Hard
ID
35%
25%
25%
15%
41200
50
55
12
48
809385
50
9
55
54
1046985
29
63
2
13
1051598
64
20
35
6
1073667
62
53
15
51
1076675
30
28
44
38
1077545
46
36
16
38
1090650
27
17
63
10
1096475
7
35
34
54
1097146
64
12
57
60
1109492
40
25
42
18
1109892
14
34
49
51
1115281
33
45
35
18
1117174
1
21
37
48
1118351
3
36
32
58
1130815
1
37
31
60
1133142
3
52
4
13
1135819
27
32
47
48
1138124
1
39
28
6
1138126
30
61
4
18
1143703
50
23
37
10
1145342
46
56
11
41
1147146
29
47
21
22
1149140
46
24
39
13
1152389
29
31
45
41
1153136
7
43
25
10
1153244
33
2
19
41
1174131
30
49
20
38
1174397
64
52
16
54
1174921
27
45
23
18
1175750
14
16
61
8
1178971
40
57
9
38
1186462
14
44
24
13
1190642
46
5
53
51
1191908
33
21
32
60
1193529
1
61
37
41
1193733
3
32
28
18
1194054
27
39
4
10
1194131
64
25
49
48
1195924
7
2
20
54
1203542
30
52
31
58
1208345
40
16
23
6

A team of UC Davis entomologists and chemists isolated an unknown compound, which they coded as "UNX". It was found to act as a trail pheromone in the crematogaster spp. Provide a structure for "UNX"; and assign all of the following pertinent spectroscopic data to the corresponding features in the structure.

Weight Percent: C 73.43%; H 10.27%; O 16.30%

High Resolution molecular ion (m/z) = 98.0732

UV: λmax = 329 nm

MS

IR

13C NMR

1H NMR