Chemistry Chem 216 H, Exam 2 - University Of Michigan Page 2
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216 H W12-Exam No. 2
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III (12 points) Shown below is the akenic H region of the 100 MHz
H NMR spectrum of methyl acrylate
(5% in C
D
). Determine the chemical shifts of H
, H
, and H
and the three coupling constants involving
6
6
A
B
c
these H’s. Write your answers in the box below
IV. (12 points) The following are the observed chemical shifts and coupling constants assignable to H-1 ~
H-6 of 7-oxabicyclo[2.2.1]heptane 6.
1
H NMR (360 MHz, CDCl
)
2.73 (1H, d, J = 15.0 Hz), 2.86 (1H, ddd, J = 15.0, 6.0, 1.25 Hz), 4.27 (1H, d,
δ
3
J = 4.5 Hz), 4.38 (1H, ddd, J = 5.0, 4.5, 1.25 Hz), 5.00 (1H, dd, J = 6.0, 5.0 Hz), and 5.05 ppm (s, 1H).
On the basis of the above NMR information and using the coupling constant information given below, assign
all chemical shifts to each of the six hydrogens (H1 ~ H6). Note that there is a W-letter coupling between 3-
exo-H and 5-H.
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