Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter 2009	Quiz 13

1. (1 pt) What bond would be responsible for the highest frequency stretching vibration in the molecule shown below?

O-H

2. (1 pt) How many C-13 absorptions would be expected for the compound below?

6

3. (1 pt) At what m/z values would the M and M+2 peaks appear for the following?

C4H7Cl , M = 48+7+35 = 90 , M+2 = 92

4. (1 pt) Which compound would show the longest wavelength absorption in uv-vis?

the tetraene on the far right

5. (6 pts) Compound X (C8H8) adds one equivalent of HBr to give compound Y.
Compound X adds one equivalent of Br2 to give compound Z.

Identify compounds X, Y, and Z.
Assign the NMR absorptions to specific hydrogens.

Compound Y proton NMR spectrum:
7.5 ppm, 5H, multiplet
3.7 ppm, 1H, quartet
1.9 ppm, 3H, doublet

Compound Z proton NMR spectrum:
7.5 ppm, 5H, multiplet
3.8 ppm, 1H, triplet
3.2 ppm, 2H, doublet

5H multiplets are the aromatic H
1H is the benzylic CHBr
3H is the methyl in Y
2H is the methylene in Z