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Problem_Set_6 - difference 4 Oxidation of 4-hydroxybutanal...

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Chem 358 Spring 2007 Problem Set #6 Text Problems Chapter 19 : 19 .37, 40, 43, 44, 46, 47, 49, 53, 55, 56, 64 Additional problems 1. Propose a practical laboratory synthesis of the following molecules beginning from the indicated starting materials. You may use any other organic reagents you wish. OH Br from (a) OH OH OH O from (b) H 3 C O H O H OH from (c) 2. What carbonyl compound and phosphonium ylide pair are needed to synthesize the following compounds? CH CH CH 2 CH 2 CH 3 3. Equilibrium between a typical ketone and its corresponding hydrate strongly favors the ketone. For cyclopropanone, however, equilibrium strongly favors the hydrate. Provide a plausible explanation for this
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Unformatted text preview: difference. 4. Oxidation of 4-hydroxybutanal with PCC does not produce the expected dialdehyde. Instead a cyclic compound called a lactone is formed. Explain this result. HO H O O O PCC CH 2 C l2 N H CrO 3 Cl PCC = 5. Alcohols react with ketones in the presence of an acid catalyst to form acetals. In a similar manner thiols also react with ketones to form thioacetals. This reaction is best catalyzed by Lewis acids, such as BF 3 or ZnCl 2 . Suggest a plausible mechanism for the BF 3-catalyzed reaction of CH 3 SH with butanal to form the corresponding thioacetal. H O H CH 3 S SCH 3 BF 3 Ether + 2 CH 3 SH + H 2 O...
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