Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter 2008	Quiz 13

1.  (2 points)  Give the molecular formula and the index of hydrogen deficiency (IHD) for benzene.  For the value you calculate, explain how the molecular structure fits that value.

C6H6

IHD = 4

1 ring + 3 pi bonds

2.  (2 points)  Describe the expected H NMR and C NMR spectra for benzene, including the expected chemical shift range and the multiplicity of each peak (do not assume there has been proton decoupling in the spectra).

H NMR: singlet, 6.5 - 8.5 ppm

C NMR: doublet, 110 - 175 ppm

3.  (6 points)  Identify the unknown compound based on the following data.  For each item of spectroscopic information, indicate what structural conclusion you can draw.
Identify each of the lettered absorptions with the hydrogens in the final structure.

Molecular formula:  
C10H14O                                Calculated IHD  =  ____4____

IR spectrum:
no significant peaks higher than 3100 cm-1           __no O-H bonds__
no significant peaks between 1700 and 2700 cm-1         __no C=O bonds_

H NMR spectrum:
         a         7.1 ppm,  5H,  multiplet
         b         3.7 ppm,  1H,  quartet
         c         3.4 ppm,  2H,  quartet
         d         1.9 ppm,  3H,  doublet
         e         1.6 ppm,  3H,  triplet

Mass spectrum:        
parent molecular ion at         (m/z) =  150      _molec. weight = 150_
large peak at          (m/z)  =  105                   _stable benzylic cation (see below)_