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234-E4-SP08 - needed to go to completion without excess...

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CHEM 234 Exam 4 Spring 2008 Name: 1. (32 points) Predict the product(s) for the following reactions. If more than one product is likely to be formed in significant quantity, indicate which is the major product. Where stereoisomers are possible, clearly show all stereoisomers formed. A) B) HO OH O - K + (1 equivalent) Br C) D) HI H 2 / Pt
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2. (16 points) Predict the MAJOR product for the following reactions. You do not need to show all stereoisomers. A) B) 1) BH 3 :THF 2) H 2 O 2 , OH - 3. (10 points) CORRECTED : A compound with the formula C 8 H 14 is subjected to ozonolysis to gives the structure below. What was that starting compound? H 2 O H 2 SO 4 (catalytic) H O O
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4. (10 points) For the following reaction, provide a complete, detailed arrow-pushing mechanism to get from the reactant to the final product. (Sufficient NaNH 2 is present for the reaction.) 5. (6 points) How many equivalents of NaNH 2 are required to carry out the following reaction. (Give the precise number
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Unformatted text preview: needed to go to completion, without excess.) Briefly explain. Br Br H 3 C C C CH 3 6. (12 points) Clearly indicate the MAJOR final product(s) of the following reaction including all stereoisomers. Draw a complete arrow-pushing mechanism for the formation of one of the stereoisomer products. Clearly indicate stereochemistry and charges at each step. Br 2 OH 7. (14 points) Using the indicated starting materials as your only source of carbon atoms, outline a synthesis for the following molecule ( cis-isomer only). You may use any other required reagents. Br Starting Materials Final Product BONUS: (8 points) Show a detailed, arrow-pushing mechanism for the full reaction in question #2B. The mechanisms for both reaction steps must be correct to receive credit....
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