CH232_1997SPRING_EXAM2__[0]

CH232_1997SPRING_EXAM2__[0] - compound(C with chromic acid...

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Organic Chemetry CH232 A p r * 1997 Second Examination 1. Show how one may carry out the tollowing conversions in good yields : (a) B rCH 2 CH 2 CHO - —*> NCCH 2 CH 2 CHO (b) CH 3 CH 2 CH 2 CH 2 CHCH 2 CH 2 CHO - —>- CH 3 CH 2 CH 2 CH 2 £CH 2 CH 2 CHO OH ° 2.Show how one may synthesize the following compound , using five carbons or fewer along with any inorganic reagents you may need . OH p=c" H* " H S.Compound (A) CyH 1 eO , reacts with sodium dichromate in aqueous sulfuric acid to give compound (B) / \ C 7 H 14
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Unformatted text preview: compound (C) with chromic acid gave compound (D) C g H 14 O. Write structures for (A) through (D). . » '^1 o> 5. Consider the reduction of (R)-3-phenyl-2-pentanone by sodium borohydride . After the reduction is complete, the mixture is separated by gas-liquid chromatography into two fractions . These fraction contain isomeric compounds, and each isomer is optically active. What are these two isomers, and what is the stereoisomeric relationship between them ? ' , c\ 6 . Using only formaldehyde and acetaldehyde ( and any other inorganic reagents necessary ) synthesize V. t h e following compound : HOH 2 C —OCH 2 OH CH 2 OH...
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