Chemistry Chem 216 H, Exam 2 - University Of Michigan (Page 5 of 5) in pdf

Chemistry Chem 216 H, Exam 2 - University Of Michigan Page 5

Name__________Key________________

216 H W12-Exam No. 2

Page 6

VI. (continued)

(1) (1 point) What is (are) the unit(s) of unsaturation of this compound?

_____Five_________

(2) (2 point) What does the IR information tell you in terms

of an O-containing functional group in this molecule?

The presence of ____Ester____ group.

(3) (2 points) What does the IR and

H NMR information tell you in terms

of an N-containing functional group in this molecule?

The presence of

____NH

_____ group.

(4) (2 points) What does a pair of doublets in the 6.5-8 ppm region of the

H NMR spectrum tell you in terms

of the substitution pattern of the benzene ring?

__1,4- or para-disubstituted

benzene___

(5) (13 points) Draw in the box below the structure of the compound (4 points) and assign all

H peaks by

writing the chemical shift values next to the corresponding nuclei (9 points).

7.9 ppm

6.6 ppm

4.2 ppm

1.0 ppm

4.0 ppm

6.6 ppm

1.8 ppm

7.9 ppm

VII. (10 points) The chemical shifts of H-1~H-6 and coupling constants involving these 7 Hs of tetraacetate

7 are summarized as follows.

δ 2.03 (1H, ddd, J = 13.4, 12.2, 10.5 Hz), 2.33 (1H, ddd, J =12.2, 4.6, 3.3 Hz), 3.04 (1H, ddd, J = 13.4, 4.0,

3.3 Hz), 5.14 (1H, ddd, J = 10.5, 10.5, 4.6 Hz), 5.15 (1H, dd, J = 10.5, 2.5 Hz), 5.38 (1H, dd, J = 4.0, 3.0

Hz), and 5.40 (dd, 1H, J = 3.0, 2.5 Hz) ppm.

On the basis of the above NMR information, write the chemical shift of each of H-1 ~ H-5 in the box next to

the corresponding H. Note that two C-6 H’s have already been assigned. No W-letter couplings are

observed in 7.

Chemistry Chem 216 H, Exam 2 - University Of Michigan Page 5