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widenhoefer_2 - Chemistry 152.2 Organic Chemistry Exam 11...

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Unformatted text preview: Chemistry 152.2 Organic Chemistry Exam 11 March 7, 2002 NAME (Last, First, M.I.): initial of last name Instructions ' Please fill in your name in the space above I Print the initial of your last name in the box above - Sign your name under the Honor Code acknowledgment - DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO - Answer questions in the spaces provided * This exam is worth 150 points * The exam period is '5 minutes. Duke Honor Code Acknowledgment: I certify that I have neither given nor received assistance of any kind in the completion of this examination. Signature 1) (15 points) Reaction of methanol with epoxide A under acidic conditions forms exclusively methoxy alcohol B. regiocherrfistry of the ring-opening. Provide an arrow—pushing mechanism for the conversion of A to B and explain the p \ A '3 Odb'gu ll 0H 0L1 --- 7 Mach 6" 43%; u 2) (15 points) Treatment of benzoic acid with excess butylmagnesium bromide followed by work—up with sulfuric acid formed 1-phenyl-1~pentanone as the exclusive product. Provide a mechanism that explains this result. UN‘STAla It; “702m of— 0 I'Fllfly/ -/- 7mm. .1. H2 0 3) (15 points) Draw the products formed from the reactions shown below. 4) (15 points) Draw a reaction coordinate diagram for the base-catalyzed hydration of benzaldehyde to phenylmethanediol. Your reaction coordinate diagram should include the reactants, products, and any relevant intermediates. Assume the first step is rate-limiting and label your diagram with AG and AG? 5) (20 points) Oxaloyl chloride (C202C12) reacts with benzoic acid in much the same way as does thionylchloride to form benzoylchloride, carbon dioxide, carbon monoxide and chloride ion. Provide an arrow pushing mechanism to account for this transformation. 0 ¢JLCI+ C°L+Co+ C10 6) (20 points) Provide an arrow pushing mechanism for the acid-catalyzed decomposition of the ethylene glycol aceta] of cyclohexanone. .A + Co fl- O=° + N //’ 7) (20 points). Provide the product or reagents required to complete each of the following transformations. CH2N2 ? ‘3" UK ¢J Pic": Me " Me H NH3IH20 8) (15 points) Benzimidic acid, formed in the acid- or base—catalyzed hydrolysis of benzonitrile, is unstable and tautomerizes to benzamide, which is ultimately hydrolyzed to benzoic acid. Provide arrow pushing mechanisms for the tautomen‘zation of benzimidic acid under both acidic (H3O+) and basic (OH‘) conditions. NH O benzimidic acid benzamide ' * i— d,» _u m K’HQP .i m n 'H J ‘ "—0 cf -0 —v d 6H (’— ¢ "/"\(5°—-'Lnl‘L . ""- .- ,; ¢ 9a,. H29 ' 01.19 f 10 0 9) (15 points) Attempted synthesis of (S)-2—hydroxypropi0nate from reaction of (R)—2—br0m0propi0nate with hydroxide ion instead formed (R)-2—hydr0xypropionate as the exclusive product. Explain. O 0 Me _OH__,.. Me$ _ .. 0' 0 Br 0H /// E: \. f H0 r O J J. 0 B rfi _ 3A2 M X .\ 0 u!” *5. '—'"-‘—" 7 H /\O (‘Nvepsffih o H 0 3 M? ' \A69 0 - ==~ xx ._ M H 0'4 11 ...
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widenhoefer_2 - Chemistry 152.2 Organic Chemistry Exam 11...

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