Exam1.2003

Exam1.2003 - Chemistry 212 Name Examination 1 . February...

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Unformatted text preview: Chemistry 212 Name Examination 1 . February 19, 2003 1. [20] Provide the structural formula for each of the following compounds. a) The wateresoluble isomer of (341-1100 that exhibits a strong, broad absorption near 3450 cm'1 in its infrared spectrum but does not react with chromic acid. b) The common solvent which is an isomer of (341-1100 that produced the NMR spectrum shown. 3.0 2.5 2.0 1.5 1.0 PPM 4 .0 3.5 ‘ ' ’ 75 . B 51-0 integral values c) An isomer of C4HSO that reacts with both 2,4—dinitrophenylhydrazine and chromic acid. 01) When dissolved in water, trichloroethanal (chloral) exists primarily as its hydrate. Give the structure of chloral hydrate. e) The enamine produced by the reaction of 3-pentanone with dimethylamine. 2. [25] Provide a detailed, step—by—step mechanism for the following reaction. OCH3 ¢O excoess CH3OH OCH3 trace HCI 5 3. [20] Provide a detailed, step-by—step mechanism for the following reaction. 0 H o I H GAGE" QHH " ———————> 4. [35] Provide structures for Compounds A, B, C, D, E, F 8.2: G. Br Mg metal H2 :0 H. 0’" pyridinium chlorocln‘omate ___—...—). ’ J ) anhydrous ether A B CH7 Cb C P1313 E triphenyl phosphine F n—butyl lithium G anhydrous ether THF THF D + G —> 1,2—diphenylethene The H—NMR and IR for Compound C are provided on the next page. The molecular formula of Compound D is C7H6O. The mass spectrum for E has a molecular ion peak (m/ e = 170) and an M+2 peak. with equal intensity. Compound G is an ylide. B Proton NMR |__,_1 3.7 Z TRHNSNITTHNCE 88 E 5 4 , 3 *. cn a: “T ‘4 \1 integral values I aa'ea as‘ara capillarg film befueen saIf plafes HAVENUHBERS lEEB Copyrighf 1992 886.0 2 PPM ...
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Exam1.2003 - Chemistry 212 Name Examination 1 . February...

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