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Problem_Set_7 - beginning from the indicated starting...

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Chem 358 Spring 2007 Problem Set #7 Text Problems Chapter 20 : 20 .24(a), (c), (e), (f), 25, 28(c), (d), (g), 29, 31, 36(a), (c), (d), (e), (f), 37, 44, 45, 46, 48, 49, 50, 51 Additional Problems 1. (a) Write a mechanism for the esterification of acetic acid with 18 O-labeled ethanol. Show clearly the fate of the 18 O label. (b) Acid-catalyzed hydrolysis of an unlabeled ethyl propionate with 18 O-labeled water (H 2 18 O) leads to incorporation of some 18 O into both oxygen atoms of the propionic acid obtained. Explain by a mechanism. 2. (From Prelim 1, Spring 98) Propose a plausible laboratory synthesis of the following molecules
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Unformatted text preview: beginning from the indicated starting materials and any other organic or inorganic reagents. CH 2 COOH CHO from (a) OH from O OH (b) OCH 3 O Br (c) from 3. Provide the reagents (A) needed for the first step and write down the structures of products B-D. O O O 1. O 3 , CH 2 Cl 2 2. Zn/H 3 O + 3. Ag 2 O THF-H 2 O A (Reagents) 1. H 3 O + 2. NaBH 4 Ethanol C H + Heat D does not react with sodium bicarbonate C 7 H 12 O 3 C 9 H 14 O 4 C 7 H 10 O 2 B...
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