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Solns3-31-06 - CHEM 252 HONORS ORGANIC CHEMISTRY ll Spring...

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Unformatted text preview: CHEM 252: HONORS ORGANIC CHEMISTRY ll Spring 2006 Dr. David J. Lapinsky 3 / 31 / 06 Problem Session: Problems associated with enolates and enols, reactions at the a-position 1.) The enantiomerically pure cyclic ketone below loses its optical activity on standing in a solution of NaOEt in EtOH. Explain. O 2.) Suggest an efficient way to carry out the following transformations. 2a.) 0 O ©/U\ ??? ©/u\/OH 2b.) 3.) Each of the following compounds may be synthesized through alkylation of an appropriate enamine followed by hydrolysis of the resulting immonium ion. Using this strategy, provide the necessary reagents for the synthesis of these molecules. 33.) 0 3b.) DIE/V 3c.) 0 3d.) 0 4.) Explain how the following molecules can be made via aldol chemistry. «)657ij 4b.)” 0 o «)6 lo) 5.) Explain why the following molecule is difficult to make and does not exist as a stable compound. 0 O 6.) Provide a mechanism for the following reactions: 6a.) 0 HO- s— (cat) 0 0 )K/“——————* H2C=O 6b.) 00A NaOEt 0 O EtOH MOE‘I heat 0 OH 1) C)“ PCC It, 04254 ; 0 3c} 0 \ Q \ / \ ‘M\ ”if“? “5:37 + Cntk'j. ?A(C {MAM [\r ~ HEP" HE: C Ham: 1% v M Gom/ B r O kufi leJLl—DA Mm M Br < ma 0 \(W O o O 33” ()5 Nqou le—«v—‘fi ,_.____._.....7 Sf nth 0 H30 “Reba" / O A ~ N ,— 54) O ‘ I =-* \\ W A C’” Q ”(fl—«a "”117”? W “CA l R 30 as?» O\ @fla Q :1; a \\/\/ / W “M \-\L\)\'\3° 5 ® 7' daggc. cummfixe cm mot-0" “‘AS Q 9150“ 3 bani-Lee, >‘T 5 01““- S'\M'k H 3 ‘9‘- HQ) 0 we} ,. Ph \ \ '22:: (“2.1 +hen “(A >953!) / Q , (iad‘\~( OH _.--.—______________? . ‘ l "ffiu‘ongFdE-fi GI QMfi\' C... O OH [\I «a cinch A F< ®/ \_\ CH'OV‘" Q Ebm O H 60m; (WW g)’“ G) \ CO“ NsOH S\ n , \- cfi , 41C , H (as ercwo~w\ “.7 W H C E) & Oms k,“ "‘ HO / HO ® m OS¥\ 60“fo V “k" #3» \ C V” 273 A J) / Ho OH HO OH {g 601'M .06) OH L /\;‘\ H \J i“; orb A N- SO Cos (:4 ml\ H -Om5 ‘\XO*Q-Z LsAAEf (SLJ A‘ Q!~‘"‘\{S;3 H ® Jr‘ntft me. me gmflodes) H o + 60” Y C) C) EJ(O H + NAG“ E+o\ / O O ...
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