quizzes_Quiz_2 - compounds D through I in this synthesis. O...

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Chem239B Summer, 2007 Quiz #2 Prof. Sasaki ______________________________________________________________________ 1. When the compound A is allowed to stand in pentane, it is converted to a constitutional isomer B . The most likely mechanism involves an intramolecular acyl substitution reaction. Draw all steps for the mechanism. O O NO 2 H N O N NO 2 HO compound B compound A 2. Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from compound C is outlined below. Write structural formulas, ignoring stereochemistry, for
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Unformatted text preview: compounds D through I in this synthesis. O O H 3 C CH 3 O O O Ambrettolide (C 16 H 28 O 2 ) heat, trace H + 1)KOH, ethanol 2) H + compound I (C 16 H 30 O 3 ) compound H (C 20 H 36 O 4 ) acetic acid sodium acetate compound G (C 18 H 33 BrO 2 ) Zn in ethanol compound F (C 18 H 33 Br 3 O 2 ) ethanol trace H 2 SO 4 compound E (C 16 H 29 Br 3 O 2 ) CCl 4 HBr compound D (C 16 H 32 O 5 ) heat H 2 O, H + compound C CH(CH 2 ) 7 CH 2 OH HOC(CH 2 ) 5 CH...
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This test prep was uploaded on 04/15/2008 for the course CHEM 239 taught by Professor Sasaki during the Spring '06 term at University of Washington.

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