Chem 335 - Winter 1999 -
Organic Chemistry II 1. (12 points) Write a complete name for each of the following compounds, including designation of stereochemistry if it is specifically shown:
a) 
b) 
c) 
2. (15 points) Write accurate structures that illustrate each of the following:
a) dimethyl sulfoxide
b) 18-crown-6
c) sodium acetylide
d) propargyl cation
e) cis-2,4-dimethyloxetane
3. (15 points) Complete each of the following reactions
by adding the missing part:
either the starting compound, the necessary reagents and conditions,
or the final major product.
Indicate stereochemistry if it is specific.
a) 
b) 
c) 
d) 
e) 
4. (10 points) Write a complete mechanism for the reduction
of 2-butyne to
trans-2-butene using sodium metal in liquid ammonia.
Show all steps and all intermediates involved.
5. (10 points) Write a complete mechanism for the acid-catalyzed hydrolysis of methyloxirane (1,2-epoxypropane). Show all steps and all intermediates involved.
6. (18 points) Identify the unknown compound that gives
the spectral data shown on the attached pages.
Clearly indicate the assignments for each of proton NMR signals
and at least three signals each from the C-13 NMR and the mass
spectrum.
Molecular formula C8H10O
H-1 NMR: 5H singlet (7 ppm), 1H quartet (5 ppm), 1H singlet (2.3 ppm), 3H doublet (1.5 ppm)
C-13 NMR: 145, 129, 128, 126, 70, 25 ppm
Mass Spectrum: 122, 107, 79, 77
7. (20 points) Write out a sequence of reactions that could be used to accomplish each of the following conversions. Show the necessary reagents and conditions for each reaction step, but do not show mechanisms. Use acetylene and methyl bromide for additional carbons.
a) 
b) 