Chemistry 220b, Section 1

Exam 1 (100 pts)

Tuesday, February 7, 2012
Chapters 13, 15, 16

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This exam is closed book and closed notes

NOTE: It is difficult for me to give you partial credit if you do not show your work!
Neatness counts
Stereochemistry counts are indicated
Good Luck !!

Name ________________________________
page 2 of 8
1-10. Multiple Choice. Choose the best answers for the following questions. (40 pts)
1. Beers Law (or the Beer-Lambert Law) is . . .
a) a linear relationship between the intensity of a UV absorbance and the concentration
of the analyte.
b) an inverse relationship between the IR stretching frequency and the energy of light.
c) used to calculate the chemical shift () of an NMR resonance relative to that of the
tetramethylsilane standard.
d) used to derive a molecular formula from the mass-to-charge ratio of an analyte.
2. Which one of the following compounds is expected to have the longest wavelength
absorbance (max)?
a)

b)

c)

d)

3. Which structure is most consistent with the following infrared spectrum?

a)

b)

O
C

OH

c)
C

d)

O
C

OH O

OCH3
H

OCH3

4. Which of the following statements is true about the molecular ion of an analyte in the mass
spectrum?
a) The molecular ion is the mass-to-charge ratio of the analyte minus an electron.
b) The molecular ion is calculated using the average masses of each element
c) The molecular ion is always the most abundant peak in the mass spectrum.
d) All of the above, i.e., a, b, and c are all true.

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page 3 of 8
5. What is the predicted multiplicity of the indicated proton in the 1H NMR spectrum?
H

O
OCH3

a) quartet of triplets

c) quartet of quartet of triplets

b) septet of triplets

d) septet of doublet of doublets

6. How many 13C NMR resonances are predicted for the 1-phenyl-1-propanol?
OH

a) 9

b) 8

c) 7

d) 6

7. Which of the following is not a feasible method to synthesize 1-phenyl-1-propanol?

a)

Mg(0),
THF

Br

b)

OH
H3O+

OH
H3C-Li

H3O+

THF

c)

OH
H

H3CH2C-MgBr

H3O+

THF

d) none of the above, i.e., a, b, and c are all feasible methods to synthesize 2-phenylethanol

8. Which of the following is the best way to convert cyclopentene to trans-cyclopentane-1,2diol?

a)

OH

OsO4
(H3C)3COOH

b)

Br2, H2O

OH
NaH, THF

OH
OH

c)

d)

O3

NaBH4

then Zn(0)
H3CCO3H

OH
OH

H3O+

OH
OH

Name ________________________________
page 4 of 8
9. Which is the best reagent for carrying out the following reaction?
O
OH

a) NaBH4

c) H2Cr2O7, H3O+

b) NaIO4

d)

ClCrO3 , CH2Cl2
+N
H

10. Which of the following is the best way to synthesize phenyl butyl ether?
Hg(OAc)2

OH

a)

b)

c)

then NaBH4
NaH, THF

OH

OH

OH

Br

H2SO4

Br

d)

OH

NaH, THF

11. With respect to its 1H NMR spectrum, identify all sets of equivalent protons for 1-penten-3ol? (8 pts)

eH
aH d
H

aH
aH

hH

Hg
bH cH

fH

Name ________________________________
page 5 of 8
12. Give the major product for each of the following reactions. Clearly indicate
stereochemistry as necessary. (12 pts)

H2Cr2O7, H3O+
OH

OH

LiAlH4, ether
OCH3

OH

then H3O+

NaOH, H2O

SH

OH

H S

(2S)-bromobutane

13. The following transformations cannot be done in a single step. Complete the following by
providing the correct reagents and the structure of the intermediate. (18 pts):

Cr2O7
OH

N
H

Li
O

THF, then H3O+

OH

O
OH

a) NaH, THF

LiAlH4, ether
then H3O+

b)
OH

Br
O

Name ________________________________
page 6 of 8
14. Diethyl ether is produced from the reaction of ethanol and a protic acid catalyst (i.e.
H2SO4). Provide a detailed, stepwise mechanism for the reaction. (10 pts)

H3CH2C-OH

H3CH2C-OH

O
H O S O H
O

O
H O S O H
O

H3CH2C-O-CH2CH3

H2O

H3CH2C-OH2

H3CH2C-OH
- H2O

O
O S O H
O

H3CH2C-O-CH2CH3

H3CH2C-O-CH2CH3

O
H O S O H
O

Name ________________________________
page 7 of 8
15. A molecule with a molecular formula C11H14O2 has the following infrared, 1H and 13C NMR
data. Provide a structure that is consistent with the data. Please circle your final answer.
(12 pts)
5 degrees of unsaturation
IR: -OH stretch, no C=O

H NMR: 3 aromatic protons ( = 6.88, 6.75, 6.65) trisubstituted benzene, 6.88 is a singlet,
therefore two of the substituents are meta to each other; 2 vinyl protons

13

C NMR: 11 13C resonances, No C=O, 8 resonances in the aromatic/vinyl region

(ppm) = 147.0
145.5
130.8
OH
130.0
OCH2CH3
122.6
H
117.2
113.1
H
H3C
112.0
64.0
or any 1,2-4 isomer
18.2
14.9

Name ________________________________
page 8 of 8

___________________________________________________________________________________
Problem

1-10:_______ (40 pts)

11:________ (8 pts)
12:_______ (12 pts)
13:_______ (18 pts)
14:_______ (10 pts)
15:_______ (12 pts)

Total out of 100: _________