QUIZ #1/ Chem 227/ 2009

The Quiz is to be done independently.
You may consult both print and on-line references, EXCEPT for "Ask Dr. Structure" and other living, breathing entities.

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) Consulting the link below for spectroscopic data, provide structures for each of the problems on the form with accompanying justification (peak assignments).

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

 

Easy

Medium

Medium

Hard

ID

35%

25%

25%

15%

101088

50

55

12

48

829186

50

9

55

54

861349

29

63

2

13

906779

64

20

35

6

912112

62

53

15

51

914431

30

28

44

38

1001424

46

36

16

38

1029871

27

17

63

10

1035979

7

35

34

54

1049440

64

12

57

60

1059997

40

25

42

18

1090788

14

34

49

51

1104182

33

45

35

18

1108961

1

21

37

48

1109537

3

36

32

58

1109974

1

37

31

60

1111645

3

52

4

13

1112120

27

32

47

48

1117906

1

39

28

6

1125994

30

61

4

18

1127524

50

23

37

10

1132408

46

56

11

41

1134222

29

47

21

22

1136755

46

24

39

13

1144529

29

31

45

41

1145146

7

43

25

10

1145787

33

2

19

41

1148149

30

49

20

38

1148251

64

52

16

54

1149469

27

45

23

18

1164076

14

16

61

8

1174791

40

57

9

38

1197633

14

44

24

13

1214490

46

5

53

51

3) A UC Davis entomologist isolated an unknown compound, which she coded as "UNI". It was found to act as a trail pheromone in the crematogaster spp. Provide a structure for "UNI"; and assign the spectroscopic data to the corresponding features in the structure.

The following data was obtained for the compound.

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

MS: molecular ion: m/z 98; base peak: m/z 69; High Resolution molecular ion (m/z) = 98.0732

UV: λmax = 329 nm

IR: 1705 cm-1 (s); 2800 cm-1 (moderate)

13C NMR (ppm): 14.1(q); 22.8(t); 35.0(t); 131.0(d); 158.0(d); 190.0(d)

1H NMR: 9.4ppm (1H) doublet J=7Hz; 6.8ppm (1H) multiplet, J1,2=16Hz coupled to 6.1ppm (1H) doublet of doublets J2,1=16Hz and J= 7Hz respectively; 2.2ppm (2H) multiplet; 1.7ppm (2H) multiplet; 1.0ppm (3H) triplet