Organic Chemistry III
	Professor Carl C. Wamser
Chem 336 - Spring Term	Exam 1 Answer Key

1.  (15 points)  Write complete names for each of the following:

a) 

N-ethyl-3-methylbutanamide

b)

methylethenyl o-hydroxyphenylacetate

c)

3-cyclohexyl-3-oxopropanoyl chloride

d)

(E,R)-7-hydroxy-4-octenenitrile

e)

sodium cis-3-bromocyclobutanecarboxylate

2.  (15 points)  Write complete structures for the following:

a)  2,4,5-trichlorobenzonitrile

b)  the enolate anion (best resonance form) of 2,4-pentanedione

c)  the Claisen condensation product from ethyl propanoate

d)  p-methylbenzyl p-methoxybenzoate

e)  malonic anhydride

3.  (15 points)  Complete the following reactions by adding the missing part, either the necessary reagents and conditions or the final major product.

a) 

b)

c)

d)

e)

4.  (15 points)  Write a complete mechanism for the acid-catalyzed reaction below.
Show all steps and all resonance forms for any intermediates involved.
You may use H+ and  -H+ to show proton transfer steps.

5.  (20 points)  Show how to synthesize the compound below.  EVERY carbon-containing compound you use must come from either malonic ester or ethanol.

6.  (20 points)  The Claisen condensation is fully reversible.  Illustrate the reversal of a Claisen condensation with the compound shown below.  Write a complete mechanism, including electron-pushing arrows.

In a similar manner, beta-diketones can be cleaved at their alpha position, as shown below.
Write a complete mechanism, including electron-pushing arrows.