E2,241b,S07 - EXAM 2 CHEMISTRY 241b March 8, 2007 Dr....

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EXAM 2 CHEMISTRY 241b March 8, 2007 Dr. Spurgeon ANSWER KEY __________________________________________________________________________________________ 1. (15 points) Complete the following questions by providing the requested information: a. (5 pts.) Circle the structural formula below that will cyclize to give the insect pheromone frontalin: b. (10 pts.) The following reaction scheme has one fatal flaw - propose an acceptable alternative reaction scheme that would provide the product shown: CHO OH OH O O O O O Frontalin OH O OH O O HO HO CH 3 H O O H 3 C H 3 O + Product Br H O HOCH 2 CH 2 OH cat. H + Br H O O 1. Mg, ether 2 CH 3 O H 3 C
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2. (18 points) Provide detailed reagents for the following transformations - if several steps are required, be sure to label each step - and just writing 'Jones' reagent' is not acceptable. Don’t worry about any side-reactions or intramolecular reactions, just pay attention to the functional group transformations shown. 3. (7 points) Provide the necessary information. a. Identify the reagent that you might use to convert an ester to an aldehyde. _________________________ b. Acidic cleavage (i.e. HI) of t-butyl isopropyl ether will give what alcohol? _________________________
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E2,241b,S07 - EXAM 2 CHEMISTRY 241b March 8, 2007 Dr....

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