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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 appropri Please 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. 01. i CH,CH2OH(xs) CH, H2CO2C H° 02. 03. i `OCH3 PhMgBr OCH, 04. ,CO2H I)SOCI2 05. OF D H' 06. OF Ph2P=C(CH3)2 07. Br i)Mg.Et_O il)CO2 ii)CH_Li 08. PhNH, H° 09. H,C. LiAlH, Note: Please draw the proper stereochemistry of this reduction Molecular models wil help. 10. i)NaBH4 iol 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 is 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 factor amides? SEPUCTURE (RC=O)NH. that extra group have pK, values in the range 9-10, What impounds that 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) i)Pd/Pb/BaSO, 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) law, Ph,P=CH2 A B st H2/Ni D E c It to

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