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Chem239A, Final Exam#1 - efficient synthesis of Apetinil...

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CHEM 239A Summer, 2009 FINAL EXAM #1 Name . Prof. Sasaki 90 points TOTAL Good Luck! Note: Only answers in the box will be graded. ______________________________________________________________________ 1. (30) (a) Draw the structure of D-tyrosine and L-serine. Use the 3D representation below to indicate the stereochemistry of each compound. D-tyrosine L-serine (b) DL-Glutamic acid (a racemic mixture of D- and L-glutamic acids) has been synthesized from diethyl acetamidemalonate in the following way. N H CO 2 Et O CO 2 Et + CN reagent(s) G (C 12 H 18 N 2 O 5 ) conc. HCl reflux 6 hr DL-glutamic acid (i) Draw the structure of compound G. (ii) Provide a reagent(s) in the first step. (c) Show how you would prepare DL-phenylalanine by the same protocol.
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CHEM 239A page 2 Name . 2. (30) Apetinil, an apetite suppressant, has the structure shown below. Propose an
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Unformatted text preview: efficient synthesis of Apetinil from the following starting material. You may use any reagents that you wish. Do not use the same reaction twice . You do NOT need to show the mechanism. Just provide appropriate reagents and necessary synthetic intermediates. NH Apetinil (a) C 6 H 5 CH 2 COCH 3 (b) CH 3 Br CHEM 239A page 3 Name . 3. (30) ) (a) When 6-chloropurine is heated with aqueous sodium hydroxide, it is quantitatively converted to hydroxanthine. Suggest a reasonable mechanism. N N N N H Cl NaOH, H 2 O heat N NH N N H O 6-Chloropurine Hypoxanthine (b) Predict the major product(s) for each of the following reactions. If more than one product is expected, please put all of them in the box. (i) CH 2 CN Cl H 2 O, acetic acid H 2 SO 4 , heat (ii) O O O water heat (iii) CH 3 Br NaNH 2 liquid ammonia...
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