Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter Term

Quiz 17

1.  (1 point)  Give a complete name for the following:

(S)-4-oxo-2-phenylpentanal


2.  (2 points)  Complete each of the following reactions by adding the missing part:

a)
b)


3.  (3 points)  in the synthesis of 1-hexene from pentanal, the extra C could come from either a Wittig reagent or a Grignard reagent (followed by dehydration).
Starting from pentanal and bromomethane, show the steps needed for each synthetic sequence.  Predict which would be preferred and explain why.


4.  (4 points)  Write a complete mechanism for the hydrolysis reaction below. 
It will be the exact reverse of the mechanism of formation of that product. 
Show all steps and all resonance forms for any intermediates. 
Electron-pushing arrows are optional.