Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter 2006	Quiz 13

Interpret the data shown below and identify the unknown compound. The compound has formula C11H16O .

(1) Calculate an index of hydrogen deficiency.

IHD = 4

(1) Calculate where the parent molecular ion would appear in a mass spectrum.

MW = (11 x 12) + (16 x 1) + (1 x 16) = 164

(2) The infrared spectrum shows no peaks in the region from 4000-3100 cm-1 and none in the region 2000-1700 cm-1. Explain what you can conclude from these data.

No O-H bonds and no C=O bonds

(6) The H-1 NMR spectrum is as follows. Correlate each absorption (by letter) with particular hydrogens on your final structure.

a 1.0 ∂ , 3H, triplet
b 1.5 ∂ , 3H, singlet
c 1.8 ∂ , 2H, quartet
d 3.6 ∂ , 3H, singlet
e 7-8 ∂ , 5H, broad multiplet