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Penn 241q3-06 ans - CHEM 241-601 Name Quiz 3 85 pts...

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CHEM 241-601 Name________________________ Quiz 3, 85 pts University of Pennsylvania Signature___________________________ 5 December 2005 due 12/12/05 at 12:00 noon in the chemistry office You are allowed to use your notes , text and copies of slides from my powerpoint lectures. You are not allowed to use the internet, our web site, copies of other pages from our web site, Wade’s answer book or eachother. Your signature verifies this. Read the questions carefully. I would advise working the problems on scrap paper and then transcribing them neatly onto this paper. 1.(15) Draw the following compounds: a) (E) 3-(cyclopent-3-enyl)-2-hepten-5-yne b) 1(R),3(S) 3-allyl-3-(2-propynyl)cyclopentanol OH c) Name the following compound: OH Cl 2(S)-chloro-6-cyclopropylhex-5-yn-3(S)-o or ... 5-hexyn-3-ol 2(S),3(S) 2-chloro-6-cyclopropylhex-5-yn-3-o or 2.(15) An unknown, optically active hydrocarbon A has a molecular formula of C 10 H 16 . Upon treatment with H 2 on a Lindlar catalyst, compound B , C 10 H 18 , is formed. Catalytic hydrogenation of A over a standard 1% Pt on graphite catalyst affords compound C ,
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