test 302-1s08 - solutions

test 302-1s08 - solutions - Name: ______ Solutions...

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Unformatted text preview: Name: ______ Solutions _________ Chemistry 302 Test 1 February 5, 2008 (104 pts.) 1. Name the following. (4 pts. each = 8 pts.) (a) (b) OH OH OH OH H 3 C OH 4-hyroxymethylcyclohept-5-ene-1,3-diol 5-(1-hydroxyethyl)-7-methylbicyclo[2.2.1]hept-2-en-7-ol 2. Starting with any compounds having only five carbons as your source of carbon, use any other reagents you need to give a concise synthesis of the compound below. (12 pts.) Br Br O O DIBAH H O MgBr 1 1 OMgBr H + OH PBr 3 3. Alcohol 1 can be converted to compounds A-H. Match the reagents below with the proper conversion. (3 pts. each = 24 pts.) A B C D E F G H H 3 CO HO O HO HO o HO O O OH OH Reagents A PCC B 1) NaH 2) CH 3 I C Lindlars D LAH/AlCl 3 E [H 2 SO 4 ]/ F Acetyl choride/Et 3 N/Et 2 O G Hg 2+ /H 2 SO 4 /H 2 O H 1) Lindlars 2) OsO 4 /H 2 O 2 2 4. Using mechanisms show clearly how the product is formed from the starting material. (12 pts.) OH OH H + heat O OH OH H + heat O OH OH O OH OH 2 OH-H 2 O OH OH HO ~R HO-H + 5.5....
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test 302-1s08 - solutions - Name: ______ Solutions...

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