Part I Predict the Product (50 pts)
A. Instructions: Give the expected major product of products in each the following
Clearly show the where propriate use of dashed lines,
stereochemistry the to wedged conditions
up or work-up that give the final neutra no reaction Expected, write
16. these reactions are also in your class notes. Please refer
can be found in the of-chapter summary section
to these resources to aidi your responses.
Note: Please draw the proper stereochemistry of this reduction Molecular models wil help.
Part II. Mechanisms and Spectroscopy (50 pts)
A. Dutch disease is caused by fungus that transmitted to clm trees by the elm bark beetle. The
female beetle locates suitable tree then releases several phefomones, including the compound
multistriatin shown below The pheromones attract the male bectles which carry the fungus thereby
infecting susceptible trees.
Multistriatin features single group the ketal. When reacted with dilute acid. multistriatin
produci with This new compound exhibits strong
IR band 1715 cm' Propose structure for this new product. (10 pts)
B. The bicyclic ketone undergoes hydride reduction with LiAIH much faster rate than the
bievelic ketolle (i.e. kp>k,) Explain this stark difference rates. Hint: Use molecular models to
help you arrive at your answer (10 pts)
6-2/4 LiAIH4 OH
C. While amides are much less basic than amines they are much acids Arnides RCONH.
have aminess . Imides
pK values in the range whefeas pK, 33-35
SEPUCTURE (RC=O)NH. that is.an extra group have pK, values in the range 9-10, What
extra factor accounts for the greater acidity imides (05 pts).
D. Nitriles (R CN) are can be partially reduced with poisoned (deactivated) Pd catalyst and the
resulting product hydrolyzed with water catalyst. This two-Step process represents very
useful functional group intercon version (FGI) Write the final product of these two steps. (10 pts)
E Methyl isocyanate (MIC) CH,N=C=0, an important industrial chemical It is also a very reactive
Predict the products that would be formed by reacting MIC with (a) ethanol: and
(b) thylamine (10 pts).
Part III. Synthesis (25 pts)
A. Give the structures for compounds A.B.D. E,and below in the following transformations of this
multistep synthesis. (25pts)
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