Name: ____________________,_________________

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July 28, 2010

Test #2

Chem151-001 Dr. Canelas

Instructions and Information - Read Carefully

Put away all papers, books, calculators, cell phones, and pagers.
You may use a model kit and a ruler; do not share your models with classmates during the test.
The time allowed for this exam is 75 minutes.
This test has 7 pages of questions (6 sheets of paper.)
The last page of your exam is a table of spectroscopy data. Please feel free to detach this for use

1.
2.
3.
4.
5.

I pledge that I have neither given nor received unauthorized aid on this exam:
_____________________________________
(signature)

Periodic Table
1

1.008

1.008

Li

Be

6.941

9.012

10.81

12.01

14.01

16.00

19.00

11

12

Na Mg
22.99

24.31

19

20

21

22

23

24

13

14

Al

Si

26.98

25

26

27

28

29

30

31

28.09

32

15

16

17

Cl

30.97

32.07

33

34

35.45

35

He 1
4.00

10

Ne 2
2 0.18
20.18

18

Ar 3
39.95

36

Ca

Sc Ti

Cr Mn Fe

Co Ni

Cu Zn Ga Ge

As Se Br

Kr 4

39.10

40.08

44.96

47.87

50.94

52.00

54.94

55.85

58.93

58.69

63.55

65.39

69.72

72.61

74.92
74.92

78.96

79.90

83.80

37

38
38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

Zr

Nb Mo Tc Ru Rh Pd Ag Cd

In

Sn Sb Te

Xe

91.22

92.91

95.94

98

01.1
101.1
1

102.9

118.7

121.8

127.6

126.9

131.3

75

76

82

83

84

85

Rb Sr
85.47

87.62

88.91

55

56

57

106.4

72

73

74

77

78

Cs Ba La

Hf

Ta

W Re Os Ir

Pt

132.9

178.5

180.9

87

137.3

138.9

88

89

186.2

190.2

192.2

195.1

112.4

114.8

79

80

81

Au Hg Tl
197.0

200.6

204.4

86

Pb Bi

Po At

Rn 6

207.2

209

222

209.0

210

104

Fr Ra

Ac Rf

(223)

227

226

183.8

107.9

261

58

59

60

61

62

63

64

65

66

67

68

69

70

71

Ce Pr

Nd Pm Sm Eu Gd Tb Dy Ho Er

Tm Yb Lu

140.1

140.9

144.2

90

145

152.0

157.3

158.9

162.5

94

95

96

97

98

164.9

167.3

168.9

173.0

175.0

99

100

101

102

103

91

92

Th Pa

Np Pu Am Cm Bk Cf

Es Fm Md No Lr

232.0

238.0

(237)

(252)

(231)

93

150.4

(242)

(243)

(247)

(247)

(251)

(257)

(258)

(259)

(260)

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

Name:__________________________,_____________________
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Score Summary:
Number

Points

/30

/36

/12

/16

/16

/20

/20

Total

/150

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

1. (30 points)
a) Please used curved arrow notation to write reaction mechanism for the following transformation:
HBr, H2O2,

Br

b) Using the axis below as a guideline, draw the proton NMR spectrum of the major organic
product shown above for the reaction in part a. Please consider the most likely chemical shifts,
multiplicity caused by coupling between protons, and integral values; clearly indicate these on
your drawing.

Test #2

Chem151L Canelas
Last Name: ___________________
Summer, 2010
2. Consider the structures shown in each part and choose the best answer. (36 points)
a) For parts I and II, choose the letter that corresponds to the relationship between each of the pairs listed
below and write it in the answer blank.
B

a) no relationship
b) constitutional isomers

E trans-1,4-dimethylcyclohexane
(most stable chair conformation)

c) different energy conformations of one molecule

F cis-1-ethyl-2-propylcyclobutane

d) stereoisomers

I) C and D ______

e) exact same molecule with the same energy

II) A and E ______

b) Determine whether each molecule is an enantiomer in the R configuration, an enantiomer in the S
configuration, or an achiral molecule (A). Please answer with R, S, or A.

H3C

Br
H3C

H3C

CH2CH3

HO

CH2CH2OH

HO

CH3

Answers:

c) Complete the Fischer projections by drawing the atoms or groups (H or OH) attached to the
horizontal bonds. Then, compare these structures and circle their relationship below.
Compound X:
H

OH

Compound Y:

CH

O
H

O
H

OH

CH

H OH

CH3

HO H

CH3

Circle Relationship Between X and Y:

Identical

Constitutional isomers

Enantiomers

Diastereomers

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

3. Draw the following compounds: (12 points)

a) Most stable chair conformation of

H3C

CH3
CH(CH3)2
CH3

b) cis-bicyclo[3.3.0]octane

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

4. For the reactions shown below, draw the structure of the starting material or major organic
product(s), whichever is missing. Please carefully denote configuration of chiral carbons using linewedge-dash notation, if necessary; if a reaction is stereoselective (syn- or anti- addition) and a racemic
mixture results, then please show both products for this exercise. "D" is deuterium, an isotope of
hydrogen that behaves similarly. Reaction mechanisms do NOT need to be shown. (16 points)

a.
Cl2

b.
1. BD3, THF
2. H2O2, OH-

c.

1. O3
2. (CH3)2S

O
H
O

d.
OH
H-O-O-H, hv

HO

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

5. 1,2,3-trifluorocyclopentane has two different meso stereoisomers. Complete the exercises or answer
the questions below. (16 points)
a) Starting with the template below for each, complete the structures by filling in the missing
fluorines and hydrogens for each of the two different meso forms of 1,2,3-trifluorocyclopentane.
(Please note: one fluorine is shown to get you started; please fill in the other 2 F and 3 H atoms
on each line-wedge-dash structure.)

b) On your drawings above, draw an asterisk next to every carbon that is a stereocenter.
c) Pick ONE of the stereocenters youve designated and clearly indicate its absolute configuration (R
or S.) Please make sure you clearly indicate which carbon you have assigned.
d) Would a solution of the compound youve completed on the left rotate plane polarized light? Why
or why not?

e) Circle the relationship between the two structures youve completed in part a.
Identical

Constitutional isomers

Enantiomers

Diastereomers

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

6. Draw the structure of the unknown compound by solving the IR, proton NMR, and mass spectra
provided. Write information about the presence or absence of various functional groups next to
the IR spectrum for full or partial credit. Also, indicate the correlation between the signals on the
NMR and the different protons on your final structure. Please recall that a table of spectral values
is provided as the last page.(20 points)
Functional groups:

Structure of Compound:

Test #2

7.

Chem151L Canelas
Summer, 2010

Last Name: ___________________

Draw the structure of the unknown compound by solving the IR, proton NMR, and mass spectra
provided. Write information about the presence or absence of various functional groups next to
the IR spectrum for full or partial credit. Also, indicate the correlation between the signals on the
NMR and the different protons on your final structure. Please recall that a table of spectral values
is provided as the last page.(20 points)
Functional groups:

Structure of Compound:

Test #2

Chem151L Canelas
Summer, 2010

Last Name: ___________________

Typical Values of IR Stretching Frequencies:

Approximate Chemical Shifts of Carbons in

13

Approximate Chemical Shifts of

1
Hydrogens in H-NMR Spectra:

C-NMR Spectra