Notice to CH 242 Students
This represents the new material that will be ~50% of the Cumulative final on
Tuesday June 8th. The other review material will be similar to previous
exams/practice exams homework problems. The exam will only cover through
chapter 14. The term assignement will be handed in in written form on the final
exam day; it is unlikely we will have time for presentation HOWEVER please
produce a poster no smaller than 11 x 17 inches which represents the
contents of your presentation for submission on June 8th: this can be
similar to your written paper but in a single panel format suitable for viewing from
a distance (font no smaller than about 18pt) You could print out PowerPoint slides
if you have prepared them for the presentation or use other materials. This poster
will be in addition to your written paper and will be graded as your presentation.
In addition a class review will be available online that will add 5% to your
class point total, please check back to the WEB site and fill in this review
before the end of next week to get credit. Enter your name (NOT you
ID#) when completing the review, it will not be traced, your opinions are
anonymous, and appreciated.
CH242
True/False
Indicate whether the sentence or statement is true or false.
____
1. The highest m/z value corresponds to the molecular ion peak
____
2. A mass spectrometer can detect either cationic and radical species
____
3. arene oxides are important biological breakdown products of aromatic compounds
____
4. The base peak is always the highest peak
____
5. The β-spin state has higher energy than the α-spin state
____
6. The nucleii in an NMR experiment are in resonance with the magnetic field
____
7. Higher Rf frequencies and stronger magnetic fields give NMR spectrometers with better sensitivity
____
8. A Fourier Transform yields frequency based data from time based data
____
9. In an NMR experiment, the effective magnetic field is always smaller than the applied magnetic
field
____ 10. Diethyl ether has 4 groups of equivalent protons
____ 11. The 1H NMR peak for a phenolic proton would be relatively broad
____ 12. In 1H NMR deutrium is invisible
____ 13. You could take an MRI of a mummy if it wasn't completely dry
____ 14. The addition of a small amount of acid would simplify the 1H NMR spectrum of an alcohol
____ 15. Equivalent protons can sometimes be made non-equivalent at lower temperatures
____ 16. Proton coupling can only occur through three σ-bonds
____ 17. Proton coupling can occur through four bonds if one is a double or triple bond.
Multiple Choice
Identify the letter of the choice that best completes the statement or answers the question.
____ 18. The Heck, Stille and Suzuki and reaction have in common____
a. palladium tetra(triphenylphosphine)
b. the coupling of two carbon compounds
c. their similarity to the Gilman reaction
d. all of the above
____ 19. The reaction of an arene oxide with the hydroxide anion gives
a. an addition product
b. a diol
c. an enone intermediate
d. all of the above
____ 20. A crown ether could_____
a. solvate a cation
b. form an inclusion compound
c. be used as a phase transfer catalyst
d. all of the above
____ 21. a thiol can be
a. dimerized by oxidation
b. bridged by a mercuric ion
c. deprotonated and used as a nucleophile in an SN2 reaction
d. all of the above
____ 22. Using a copper bowl to whip your egg whites gives a nice stiff merangue because?
a. acetic acid
b. butyric acid
c. caprioc acid
d. formic acid
____ 23.
The base peak and molecular ion peaks
are what molecules, respectively?
a. CH CH CH + and CH CH CH CH CH
3
2
3
3
2
2
2
3
•
b. CH CH CH CH CH + and CH CH CH
3
2
2
2
3
3
2
3 •
+
+
c. CH CH CH
and CH CH CH CH CH
3
2
3
3
2
2
2
3
+
d. CH CH CH CH CH and CH CH CH +
3
2
2
2
3
3
2
3
____ 24.
The peaks at 122 and 124 represent what?
a. the molecular ion and the diprotonated molecular ion
b. the products of α cleavage
____ 25.
____ 26.
____ 27.
____ 28.
____ 29.
c. the products of heterolytic cleavage
d. a reflection of the isotopic distribution of bromine atoms in nature
The molecular ion peak of an alcohol is____
a. The base peak because its so stable
b. usually a doublet
c. very small because its so unstable
d. None of these responses are correct.
The mass spectrum of an unknown compound has a molecular ion peak with relative intensity of
43.27% and the M + 1 peak with a relative intensity of 3.81% How many carbons are in the
compound?
a. 4
b. 6
c. 8
d. 10
In an NMR experiment higher δ values correspond to____
a. electron poor protons
b. deshielded protons
c. higher frequency resonance
d. all of the above
In an NMR experiment lower δ values correspond to____
a. electron rich protons
b. shielded protons
c. lower frequency resonance
d. all of the above
CH3CH2CH2NO2
A B C
The order of 1H δ values from highest to lowest for this compound would be:
a. A > B > C
b. C > B > A
c. C > A > B
d. C > B = A
____ 30. Good examples of diamagnetic anisotropy include
a. the high δ values of benzyl protons
b. the high δ values of vinylic protons
c. none of these
d. both a and b
____ 31. 1,1-dicloroethane would give what 1H NMR spectrum from left to right?
a. a doublet and a singlet
b. a doublet and a triplet
c. a quartet and a doublet
d. a quartet and a triplet
____ 32. The 1H NMR spectrum of 1,2-dichloroethane gives only one singlet because____
a. equivalent protons don't couple
b. the two groups of equivalent protons are coupled
c. it has two groups of equivalent protons
d. none are correct
____ 33. In an 1H NMR experiment, a group of equivalent protons that are adjacent to a methine carbon
would give rise to a______
a. singlet
b. doublet
c. triplet
d. quartet
____ 34. Nitrobenzene would give what 1H NMR spectrum, from left to right?
a. doublet, triplet, quartet
b. quartet, doublet, triplet
c. triplet, quartet, doublet
d. doublet, quartet, triplet
____ 35. ClCH=CHCOOH
This compound gives an 1H NMR spectrum with doublets with a J value of ~9Hz
a. it is a cis compound
b. it is a trans compound
c. it is a meso compound
d. there is no way to tell
Short Answer
36. How would the following synthesis be carried out?
O
CH3
37. How would be the product of the following reaction?
O
1. CH3CH 2MgBr
2. H3O+
38. How would be the product of the following reaction?
Br
1. Mg
O
2.
3. H3O+
39. How would the following product be made?
S
C
H2
40. What would the product of the following reaction be?
I
+
(CH3CH 2CH 2)2 CuLi
CH242
Answer Section
TRUE/FALSE
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
T
F
T
T
T
F
T
T
T
F
T
T
T
T
T
F
T
MULTIPLE CHOICE
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
D
D
D
D
D
C
D
C
C
D
D
B
D
C
A
B
A
35. A
SHORT ANSWER
OH
H + heat
O
CH3
CH3
page 468
36.
OH
O
CH3
1. CH3CH 2MgBr
2. H3O+
see page 468
37.
Mg2+
Br
MgBr
Br -
O
Mg
H+
O
OH
38.
OH SH
39.
40.
S
see page 465 problem #26
see page 470
+
Br
CH2
S
C
H2
Br -