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Exam_3,_2009 - 1(20 points Here as promised are some...

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1 (20 points). Here, as promised, are some syntheses. You must start with methyl acetate 1 (and you must use methyl acetate) and alcohols containing no more than four carbon atoms.You may use inorganic (no carbons) reagents of your choice and special organic reagents such as NBS, CF 3 COOOH, CH 2 N 2 , Tosyl chloride, diethyl ether, LDA, LLC, and LSMFT. from: OCH 3 O 1 make: O OCH 3 (a) (b)
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2 (20 points). Write the products of the following reactions. Mechanisms are not necessary. A "product" is something formed in substantial yield. Some (or all) reactions may not yield a product. (a) (b) OH O OCH 3 O OCH 3 O OH O OH O OH O OCH 3 O Cl O Cl O NaOEt NaOH OCH 3 O 1. LiAlH 4 2. H 3 O + /H 2 O cat. NaOEt full eq. NaOCH 3 HOEt HOCH 3 1. full eq. NaOCH 3 /HOCH 3 2. H 3 O + /H 2 O to pH = 7 1. full eq. NaOCH 3 2. H 3 O + /H 2 O to pH = 1 NH 2 CH 3 1. CH 2 N 2 2. heat (c) (d) (e) (f) (g) (h) (i) (j) H 2 OR/HOR +
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3 (20 points). Give structures for A, B, C, and D . Mechanisms are not necessary, but will probably help you get the right structures. Please also complete the sentence following E . 1. CH 3 CH 3 Cl AlCl 3 2. KMnO 4 C 7 H 6 O 2 1. SOCl 2. CH 2 N 2 C 8 H 6 N 2 O h ! C 8 H 6 O CH 3 OH O OCH 3 1. CH 3 O
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