CH232_2004SPRING_EXAM2__[0]

CH232_2004SPRING_EXAM2__[0] - a o V"' Hj — o r :X-cH...

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ORGANIC CHEMISTRY CH232 A P R I L 2004 SECOND EXAMINATION [ ( o) 1 , Give a structural formula and another acceptable name for each : (a) formaldehyde (b) Acetone (c) Benzophenone (d) acetophenone (e) diisopropyl ketone / iif) 2 . An optically active compound CeH-] 20 , gives a positive test with dinitrophenyl hydrazine but a negative test with Tollens' reagent . What is the structure of the compound ? / , p) 3 . C o n s i d e r the reduction of (R)-3-phenyl-2-pentanone with sodium borohydride . After the reduction is complete , the mixture is separated by chromatography into Iwo fractions. These fractions contain isomeric compounds , and each isomer is optically active . Write structure for these isomers and what is the stereo isomeric relationship between them ? / , $•} 4. T he structure of the sex pheromone ( attractant } of the female tsetse fly has been confirmed by the following synthesis : uj-u ,r-u *. ,-TJ a d ) * (QH_0.,P H BKH,(CH 2 ),CH 2 Br _ _ , , ^ ( C H ^ . C C H , f t (2)2Rli C " H ">
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Unformatted text preview: a o V"' Hj — o r :X-cH 3 H0 CH 3 ) 6 . Starting with two carbon reagents or fewer , show how one could synthesize the following : CH 2 OH HOHjC-cJ — CHjOH (/ (?) 7,Show how one could bring about the foliowing transformation : CH 2 OH CH=CH-C-CH, l( 8. Compound (A) C/Hi eO reacts with sodium chramate in aqueous sulfurtc acid to give (B) C/H-] 40 . When {B) is treated with NaOD / DOD at 25 degrees C for several hours, analysis shows it has incorporated two deuteriums - Compound (B) is not oxidized silver oxide. Write structures for (A) and (B). 8(a) Using the Wittig reaction show how one could synthesize (b) The Baeyer-Villiger oxidation of aldehydes yields carboxylic acids. Using benzaldehyde as a model , write a mechanism for this oxidation. 9. The treatment of 1,5-pentanediol with H 2 SO 4 /heat leads to oxane and water. H,SO 4 .heal [ ] f u o HOCH 2 CH 2 CH 2 CH 3 CH 2 OH->-< Q ^ oxane Write a reasonable mechanism for this reaction....
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This note was uploaded on 02/27/2012 for the course CHEMISTRY/ CH/ECE/PH/ taught by Professor Faculty during the Spring '08 term at Cooper Union.

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CH232_2004SPRING_EXAM2__[0] - a o V"' Hj — o r :X-cH...

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