Name: _________________________________
1. (25 points) Predict how many signals you would see in the 13C spectrum of each of
these molecules. Put your answer in the box below the molecule.
CH3 O Br Br
Br
2. (20 points) The 1H NMR of this compound should have four signals. Predict the
splitting pattern (singlet, doublet, doublet of doublets, etc) you would see for each
signal.
H H H
CH3
Br O
H
2
Name: _________________________________
3. (20 points) Below are the IR spectra for four of these eight compounds. Put the letter
of the spectrum in the box below the appropriate compound.
a) Spectra A and B refer to two of these four compounds.
O
N
OH
OH
b) Spectra A and B refer to two of these four compounds.
O OH NH2
3
Name: _________________________________
4. (10 points) Below is the mass spectrum of 2-butanone. In the boxes, explain the
large peak at 43 and the small peak at 73.
43
73
4
Name: _________________________________
5. (40 points) Here are the IR, 13C NMR, and 1H NMR spectra for an unknown with the
formula C6H10O2. Answer questions on the next page.
5
Name: _________________________________
5 continued. (40 points) These questions all refer to the spectra on the previous page.
a) How many degrees of unsaturation are in this compound?
b) Is there symmetry in this compound?
c) In the IR, what does the signal at about 1740 suggest?
d) In the 13C NMR, what does the chemical shift of the signal at about 105
suggest?
e) In the 1H NMR, what does the chemical shift of the signal at about 5.2 suggest?
f) In the 1H NMR, what does the integration of the signal at about 2.3 suggest?
g) In the 1H NMR, what does the splitting pattern of the signal at about 1.0
suggest?
h) What is the structure of this unknown?
6
Name: _________________________________
6. (30 points) Draw what you would expect to see in the 1H NMR of this compound.
Your drawing should clearly show the number of signals, their approximate chemical
shift (within 1 PPM) and the expected splitting pattern.
O
OCH3
11 10 9 8 7 6 5 4 3 2 1 0
7. (15 points) Draw the important resonance structures for this compound.
7
Name: _________________________________
8. (50 points) Predict the major organic product or products for the following reactions.
O
H2NNH2
KOH
heat
O
excess CH3OH
H+
O
Li
liquid NH3
Cl
O2N Cl
CH3O
NO2
excess H2O
O O
H+
8
Name: _________________________________
9. (40 points) Please draw a reasonable arrow-pushing mechanism for the following
reaction.
H+
H2O
O O OH
9
Name: _________________________________
Approximate IR Absorption Frequencies
–1
Bond Frequency (cm ) Intensity
O–H (alcohol) 3650–3200 Strong, broad
O–H (carboxylic acid) 3300–2500 Strong, very broad
N–H 3500–3300 Medium, broad
C–H 3300–2700 Medium
C≡N 2260–2220 Medium
C≡C 2260–2100 Medium to weak
C=O 1780–1650 Strong
C–O 1250–1050 Strong
1 13
Approximate H NMR Chemical Shifts Approximate C NMR Chemical Shifts
Hydrogen δ (ppm) Carbon δ (ppm)
CH3 0.8–1.0 Alkanes
CH2 1.2–1.5 Methyl 0–30
CH 1.4–1.7 Methylene 15–55
C=C–CHx 1.7–2.3 Methine 25–55
O=C–CHx 2.0–2.7 Quaternary 30–40
Ph–CHx 2.3–3.0 Alkenes
≡C–H 2.5 C=C 80–145
R2N–CHx 2.0–2.7 Alkynes
I–CHx 3.2 C≡C 70–90
Br–CHx 3.4 Aromatics 110–170
Cl–CHx 3.5 Benzene 128.7
F–CHx 4.4 Alcohols, Ethers
O–CHx 3.2–3.8 C–O 50–90
C=CH 4.5–7.5 Amines
Ar–H 6.8–8.5 C–N 40–60
O=CH 9.0–10.0 Halogens
ROH 1.0–5.5 C–F 70–80
ArOH 4.0–12.0 C–Cl 25–50
RNHx 0.5–5.0 C–Br 10–40
CONHx 5.0–10.0 C–I –20–10
RCOOH 10–13 Carbonyls, C=O
R2C=O 190–220
RXC=O (X = O or N) 150–180
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