CHEMISTRY 212
EXAM 1
Friday, January 24, 2003
Answer Key
1. (8) Draw the structure of each of the following molecules:
a) 3-Chloro-5-methyl-4-nitrophenol
b) meta-nitrotoluene
CH3
OH
H3C
NO2
Cl
NO2
2. (15) Name the following using IUPAC rules.
a)
b)
Br
c)
NO2
F
CH3
Cl
4-bromo-2-nitrotoluene
OH
F
NO2
NO2
4-chloro-3-fluorophenol
4-fluoro-1,2-dinitrobenzene
3. (4) True or False. The molecule shown would have 3 peaks in its 13C-NMR spectrum.
O
O
O
O
4. (8) In each of the following, show one other satisfactory resonance form. You need not show arrows.
a)
b)
N
N
5. (8) For each of the following compounds indicate how many signals would appear in its proton NMR
spectrum?
4 H sig nals
4 H sig nals
4 H sig nals
2 H sig nals
6. (4.) What splitting pattern (singlet, doublet, etc.) is observed in the 1H-NMR spectrum for the
indicated hydrogen?
CH3
H3C
CH
a) doublet
d) quintet
CH CH2 CH3
H3C
b) triplet c) quartet
e) sextet
CH2
7. (20) Show reasonable products from the following reactions. Draw the stereochemistry of the product(s) as
appropriate.
a)
KNH2
Cl
+
H3 C
b)
+
Br
Cl
+
F
F
Cl
Br
H3C
+
H3C
Br
F
c)
Et
Br
Et
Me
KOMe
Me
Et
Me
CH2
Et
+
Me
H
Cl
Et
H
Et
Me
Et
Me
Me
CHCH3
+ H
8. (12) For each of the following compounds, indicate by yes or no whether or not they contain
conjugated systems.
a)
b)
NH
c)
d)
O
No
Yes
O
Yes
Yes
NH
9. (15) For each of the following molecules, indicate the number of different types of hydrogen and the
number of different types of carbon present.
a)
O
b) H
O
3 different H
3 different C
OH
c)
H
5 different H
5 different C
3 different H
3 different C
OH
10. (9) State, in each of the following, whether or not the dienes shown would undergo the Diels-Alder
reaction.
Me
a)
b)
c) Me
Et
No
Yes
No
11. (5) In the Diels-Alder reaction below, which starting material, A, B, C or D, is required to form the
product shown?
O
O
A.
H
A-D?
B.
O
H
O
C.
O
D.
O
12. (5) The molecule shown would have which 1H-NMR spectrum ?
O
A.
B.
C.
D.
Singlets at ~7  & ~2.5, a quartet at ~2  & a triplet at ~1 
A singlet at ~7.5 , a quartet at ~1.5 & a triplet at ~4 
A singlet at ~1.75 , a quartet at ~4 & a triplet at ~1.5 
A singlet at ~7 , quartets at ~2  & 4& a triplet at ~1.5 
13. (7) Peaks in the NMR spectrum which are further to the left are considered to be
(downfield, upfield, sinister) and their locations are measured relative to a standard, namely
The
,
TMS .
standard should be [circle all which apply]: unreactive, high boiling, a molecule with many identical
hydrogens, a symmetrical molecule.
14. (6) Benzene is
(more, less, equally) stable than a typical alkene because its double bonds
are
(circular, conjugal, conjugated). If a benzene ring bears 3 substituents it is called tri
substituted and if they are attached 1,4- to one another this would be
(ortho, meta, para)
substitution.
15. (12) From among the compounds shown below, choose the one that:
a) Gives three groups of peaks in its 1H-NMR spectrum; b) Gives the simplest 13C-NMR
spectrum;
c) Has 3 peaks in its 13C-NMR spectrum.
Cl
Cl
Cl
Cl
Cl
3 peaks in proton NMR
Cl
3 peaks in carbon NMR
s implest carbon NMR
16. (3) A very broad, medium strength peak at ~3300-2400 cm-1 in an IR spectrum would indicate
A. An amine
B. An aromatic ring
C. A cyclohexene
D. A carboxylic acid
E. A ketone
17. (3) There are two key general areas in an infrared spectrum - name them.
Functional group and Fingerprint
18. (3) A strong peak at ~2900 cm-1 in an IR spectrum would indicate ?
A. A carboxylic acid
B. An alkane
C. An aromatic ring
D. An alkene
E. A ketone
19. (3) Sharp peaks at ~3300 cm-1 in an IR spectrum would indicate ?
A. A carboxylic acid
B. An amine
C. An aromatic ring
D. An alcohol
E. An alkane