1. (15 points) Write a complete IUPAC 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 for the following:
a) TMS
b) heptanoyl bromide
c) potassium p-nitrobenzoate
d) isobutyl acetate
e) ethanoic propanoic anhydride
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 products. Indicate stereochemistry if it is specific.
a) 
b) 
c) 
d) 
e) 
4. (6 points) Complete the table below by matching the proper letters to the empty spaces.
Spectroscopic Method |
Type of Molecular Energy |
Approximate Photon Energy |
IR |
C |
b |
UV |
B |
c |
NMR |
A |
a |
Types of Molecular Energy:
A - nuclear spin states
B - electronic energy
C - vibrational energy
Approximate Photon Energies:
a - 1 cal/mole
b - 1 kcal/mole
c - 100 kcal/mole
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(4 points)
The 13C NMR spectrum of cyclohexanone would be expected to have how many different absorptions?
4
Give the structure of an isomer of C3H6O that would have not have any IR absorptions in the 3000 - 3600 cm-1 range nor in the 1500 - 2000 cm-1 range.
5. (15 points) Write a complete mechanism for the acid-catalyzed hydrolysis of ethyl acetate to give ethanol and acetic acid. Show all steps and all resonance forms for any intermediates involved. Each step should show just one bond breaking or making.
6. (15 points) Write a complete synthetic sequence to illustrate how you could prepare EITHER ONE of the compounds below. You may use as starting compounds any alcohol having four carbons or fewer.
Show each reaction step with the necessary reagents and conditions, but it is not necessary to show reaction mechanisms.
CHOOSE JUST ONE
7. (15 points) Compound X is a product obtained from a reaction using ethyl benzoate and excess ethyl Grignard reagent. The NMR spectrum of X is shown on the next page. Identify the structure of compound X, indicate the specific hydrogens that correspond to each of the NMR peaks, and show the reaction that took place.
