Chemistry Chem 216 H, Exam 2 - University Of Michigan Page 3

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216 H W12-Exam No. 2

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V. (16 points) On the basis of its spectroscopic information provided below, answer the questions given

below and propose the structure of the compound, C

-1

IR (KBr): 2913-2850 (several weak peaks), 2270 (sharp, medium intensity), 1601 (s), 1745 (strong) cm

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

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

C NMR 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

C NMR information tell you in terms

of an N-containing functional group in this molecule?

The presence of

__C≡Ν or

Cyano___ group.

(4) (11 points) Draw in the box below the structure of the compound (3 points) and assign all

H and

peaks by writing the chemical shift values next to the corresponding

H and

C nuclei (8 points).

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