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Exam1.2002 - Chemistry 212 Name Examination 1 I 1[20...

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Unformatted text preview: Chemistry 212 Name Examination 1 I February 13, 2002 1. [20] Provide the structural formula for the major product of each reaction. Clearly indicate any relevant stereochernistry. O H (>20 ‘HZNCNHNHZ / acidic buffer OLOH conc. H2504 A $0 CH30' Na+ in CH3OH 1) triphenyl phosphine 2) n—butyl lithium 3) 3-pentanone 1-bromopropane ——-——————> .2. [20] Provide an appropriate starting compound for each of the following reactions: /_\ O excess HOCHZCHZOH, trace HCl MO ————-——————-—-——> H . yridinium chlorochromate H p (PCC) in CH2C12 1) Mg in anhydrous ether OH 2) 2-butanone 3) H30+ m—chloroperbenzoic acid in CH2C12 ———————————> 3. [20] (a) Provide a detailed, step-by—step mechanism for the following reaction. N—CI—I3 ' O / (j + CH3NH2 ———-——>HC1(aq)’pH:5'8 O (b) The reaction proceeds efficiently at pH = 5.8, but when the reaction is attempted using a solution with pH = 1.2 the reaction does not occur at a measurable rate. Explain this observation. 4. [20] When Compound A (C9H18) is treated with ozone (03) followed by zinc in acetic acid, Compound B (C4H80) and Compound C (C 5H100) are produced in equal quantities. Compound B reacts With 2,4—dinitrophenylhydrazine to produce a yellow precipitate, and it reacts with iodine in aqueous KOH to produce iodoform (CHI3). The H—NMR spectrum for B is given below. Compound C, Which exhibits a strong IR absorption at 1727 cm‘l, reacts with chromic acid to produce a green precipitate and pentanoic acid. WhenC reacts With dimethylamine at pH = 5.8, compound D (C7H15N) is produced. Provide structures for Compounds A, B, C, & D. H—NMR for Compound B. ' 3 2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.5 1.4 1.2 1.0 0.8 0.5 PPM Proton NMR . 21.4 30.2 integral values 31-7 $H3 (IIHs 00—? CH3 Lot—Hi) OOH I—CII—CH3 CH3 CH3 (b) No iodobenzene is produced in_the reaction. Explain this result. ...
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