fall-07-zimmerman-q6-key - 2,“qu Organic Chemistry 345...

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Unformatted text preview: 2;,“qu Organic Chemistry 345 Kti Spring 2007 Quiz 6a Name (Please Write Clearly) Give the products of synthesis as isolated after workup. 11* In ) 1) Benzaldehyde + l 3—propanedithiol ——-—-——I'- '0 _CH/3 \ 3 or r i {' 690610))..3 / CO" 57‘ 2) Benzaldehyde + Diethyl Malonate P h-CH' =7- C. EtzNH EtOH \Cove 1, 3) m ______ m ' s s 1)BuLi . €545“ [Bl/t. Y 2) Benzyl Bromlde Mt 1.. Me Ph MCLC Ch'C “'1. q? ”A _ _ Ph 4) MezC‘CH'E Ph + W NaOEt EtOH 0 O O O O 0 PM} fl Pk 65 HCI N + Pyrroiidine W 5) Benzene Azeotrope 6) Pyrrolidine + Acetophenone CHZO [0 5 Ph Pk ,CwuH \c=o ‘C(COOEt)2 ,R / 7) Et’ Urea, NaOEt E k f? ~~1+ ' b O o o 8) N 1.Benzoy| Chloride L-‘Plfi' 2. H20 workup 15‘ W W82?) 9) What base could be used to prepare LDA from Diisopropylamine? BILLi Wt (Butyllithium, Lithium Ethoxide, Lithium Hydroxide) 10) Write out the mechanism of the Knoevenagel Condensation of Benzaldehyde with Ethyl Acetoacetate (assume some base catalyst). As usual, put in all arrows, charges unshared electrons. f9 11$ B344» (9 090E p ffH éH\/ —% pk CH‘S-(OODEBg—fi Five/Vt C(C60Ci’)o (30‘ $66343 9?? fi‘q‘Q} ”—Cfi O o lam ...
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