QUIZ #1.2 / Chem 227 / 2013

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
Medium
Medium
Hard
ID
35%
25%
25%
15%
1027591
64
12
57
60
1090054
1
21
37
48
1116652
40
25
42
18
1127356
30
49
20
38
1149672
29
63
2
13
1162107
46
5
53
51
1170444
64
52
16
54
1183104
33
21
32
60
1187342
7
2
20
54
1190943
29
47
21
22
1190952
50
43
25
10
1193063
27
45
23
18
1195192
14
16
61
8
1195985
3
36
32
58
1216607
29
31
45
41
1220740
14
44
24
13
1230302
46
36
16
38
1231760
27
39
4
10
1232718
7
35
34
54
1233406
46
24
39
13
1235241
46
56
11
41
1240766
40
16
23
6
1242314
1
39
28
6
1245139
30
52
23
8
1247967
27
17
63
10
1270318
64
20
35
6
1279205
1
61
37
41
1281262
50
9
55
54
1282528
3
32
28
18
1286533
7
2
20
54
1289853
30
28
44
38
1296685
62
53
15
51
1299090
30
52
31
58
1299617
1
37
31
60
1300640
64
25
49
48
1302626
40
57
9
38
1316973
30
61
4
18
1322574
50
55
12
48
1330386
50
23
37
10
1334700
14
34
49
51
1346688
27
32
47
48
1350575
33
2
19
41
1384811
3
52
4
13
1385715
33
45
35
18

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