Name: …………………………………………………………
CHEMISTRY Final Exam
Spring 2019
Part I. Multiple Choice. Provide the best Answer (60 points)
1. 1. Which structure of molecular formula C4H8Cl2 fits both the 1H NMR and 13C NMR spectra shown
below?
2. Which signal(s) remain(s) when a DEPT-90 spectrum is run?
3. Find all the types of nonequivalent protons in the given compound.
a.
b.
c.
d.
e.
4
6
7
9
13
4. Electrophilic addition reaction of conjugated dienes that occur at high temperature and/or long reaction
times (reversible conditions) are said to be under:
a.
b.
c.
d.
1,2-control
kinetic control
1,4-control
thermodynamic control
5. Which of the following compounds is the most stable?
a.
b.
c.
d.
penta-2,3-diene
2,4-hexadiene
1,4-pentadiene
3,6-octadiene
6. Which of the following compounds would show the longest wavelength λmax in its UV spectrum?
7. In 1839, Charles Goodyear discovered a process by which both natural and synthetic rubbers are
hardened. This process is called:
a.
b.
c.
d.
diazotization
vulcanization
polymerization
condensation
8. Based on the following spectrum, what is the energy in kilojoules per mole of photons that corresponds
to the λmax?
9. Which of the following is the most likely to happen when a conjugated diene is irradiated with
ultraviolet light?
a.
The bonds between different atoms in the molecule undergo symmetric stretching.
b.
A electron is promoted from the highest occupied molecular orbital to the lowest
unoccupied molecular orbital.
c.
A electron is demoted from the lowest occupied molecular orbital to the highest
unoccupied molecular orbital.
d.
The bonds between different atoms in the molecule undergo asymmetric stretching.
10. M+ at m/z = 101 with a minor M+1 peak
a.
b.
c.
d.
C5H6Cl
C5H12N2
C6H15N
C9H12O
11. Loratidine is the active ingredient in the antihistamine Claritin®. Mass spectral analysis of loratidine
shows M+ at m/z = 382 and M+ at m/z = 384 in an approximate ratio of 3:1 in intensity. The mass spectral
data indicates that loratidine contains:
a.
b.
c.
d.
fluorine
chlorine
bromine
iodine
12. The amount of energy in infrared light corresponds to:
a.
the amount of energy needed to promote one electron from a bonding to an antibonding
molecular orbital
b.
the amount of energy needed to "flip" the spin of a 13C or 1H nucleus
c.
the amount of energy needed to strip a molecule of one electron to generate a cation radical
d.
the amount of energy needed to increase certain molecular motions, such as bond vibrations, in
organic molecules
13. C−C, C−O, C−N, and C−X single-bond vibrates ar;
4000 to 2500 cm−1
2500 to 2000 cm−1
2000 to 1500 cm−1
below 1500 cm−1
a.
b.
c.
d.
14.
a.
c.
b.
d.
15. Which of the following aromatic compounds will have largest number of signals in a 13CNMR?
a.
b.
c.
d.
1,4-dimethylbenzene (p-methyl toluene)
1,3,5-trimethylbenzene (mesitylene)
1,2,4,5-tetramethylbenzene
All produce the same number of signals.
16. Which command is aromatic?
a. I
b. II
c. III
d. IV
17. Which command is antiaromatic?
18. Which of the following could successfully undergo a Friedel-Crafts alkylation? Assume an
appropriate catalyst.
a.
b.
c.
d.
chlorobenzene reacting with benzene
2-chloroethene reacting with benzene
2-chloropropane reacting with benzaldehyde
2-chlorobutane reacting with benzene
19. To answer the following question(s), consider the reaction below:
Refer to Exhibit 17-3. The best reagents for accomplishing the above transformation are:
a.
b.
c.
d.
1.
2.
1.
2.
1.
2.
1.
2.
OsO4, pyridine
NaHSO3, H2O
Hg(OAc)2, H2O
NaBH4
RCO3H, CH2Cl2
H3O+
BH3, THF
H2O2, −OH
20. Which of the following is the least acidic alcohol?
21. The conversion of an alcohol into an alkyl chloride by reaction with SOC12 is an example of:
a.
b.
c.
d.
an E1 process
an SN1 process
an E2 process
an SN2 process
22. What is the final product of the following reaction sequence?
23. The reaction of an aldehyde with hydrogen cyanide is an example of _____ reaction.
a.
b.
c.
d.
a nucleophilic substitution
an electrophilic addition
an electrophilic substitution
a nucleophilic addition
24. α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon, as
shown below.
This reaction is called _____ reaction.
a.
b.
c.
d.
a 1,2-conjugate addition.
an electrophilic addition.
a direct addition
a 1,2-addition.
25. Consider the reaction below.
Mechanistically, the Williamson ether synthesis outlined above is:
a.
b.
c.
d.
an E1 process
an SN1 process
an E2 process
an SN2 process
26. What is the correct structure for 2-hydroxyacetophenone?
27. What is the product of the following synthesis?
28. Which none can not undergo the Michale reaction?
29. The Hell-Volhard-Zelinsky reaction:
a.
b.
c.
d.
produces an alpha-brominated ketone.
Brominates alcohols.
Produces an alpha-brominated carboxylic acids.
Oxidizes aldehydes to carboxylic acids.
30. The chemical shifts for protons at alpha-position to a carbonyl group:
a.
b.
c.
d.
e.
Are similar for all acid derivatives.
Fall between 1.3 and 1.8 ppm.
Are farthest downfield for carboxylic acids.
Are farther downfield than those alpha to a nitrile.
Fall between 3.1 and 4.2 ppm.