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Exam2.2002 - Chemistry 212 Name Examination 2 1[40 Provide...

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Unformatted text preview: Chemistry 212 Name Examination 2 ' March 22, 2002 1. [40] Provide the structural formula for the major organic product of each reaction. 0 | I CH3CH2CH2C\ + CH3OH ————> C1 0 o dilute HCl 80 °c OH 1) NaOH 2) co2 3) H3O+ ——————> . Q + NaNHg diethyl ether 0 0-c O t CH CH CH PINE SOCIZ ———>' 3 2 2 2 100 °c CHZCH3 H2CI'O4, H20 ————-> o o 1) CH3O' Na+, CH3OH ” ” 2 d d‘ t CH30CCH2CH2CH2CH2COCH3 % 1) excess lithium diisopropyl amide O 2) methyl iodide . o N—O+/\/Br——.——> _\___/ l?) \ CH O [I NaOH(aq) + CH3 CH ' 8 O °-C * (added slowly) 2. [20] Provide a detailed, step-by—step mechanism for the following transesterification reaction. Include relevant resonance structures. ‘3 ' , O OCHZCH3 trace of HCl in CH3 OH OCH3 -—-———————)- reflux at 65 °C 3. [20] Using ethyl benzoate, ethyl acetate and bromoethane as sources of carbon atoms for the product propose a reasonable synthesis for butyrophenone. Any other chemicals may be used for reactions if they do not provide carbon atoms for the product. ‘3 ‘R C C O \OCHZCH3 . 0/ \CHZCHZCH3 _______._> butyrophenone ethyl benzoate 4. [20] Provide a detailed, step-by-step mechanism for the Darzens condensation reaction that occurs with ethyl chloroacetate and benzaldehyde. Include relevant resonance structures. 3). CH CH3 CH2 0- Na+ G + CIHZCOZCHZCHB £52122; ...
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