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Problem_Set_6 - γ-butyrolactone is formed Explain this...

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Chem 3580 - Spring 2009 Problem Set 6 Text Problems Chapter 17 : 47, 48a, 49b-e, g-i, 51-53a, c, e, h, i, 54, 56 58, 60-62, 65, 69, 75-77, 80, 82, 84 Additional Problems 1. Propose a practical laboratory synthesis of the following molecules beginning from the indicated starting materials. You may use any other organic (containing no more than 3 carbon atoms) and inorganic reagents you wish. OH OH from H O from H O OH from H O OH O OH (a) OCH 3 O Br (e) (b) (c) (d) from from OH Br OH OH OH O H 3 C O H O H OH (f) (g) (h) from from from 2. Oxidation of 4-hydroxybutanal with PCC does not produce the expected dialdehyde. Instead a lactone,
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Unformatted text preview: γ-butyrolactone, is formed. Explain this result. Use chemical structures and reaction schemes to support your reasoning. HO H O O O CH 2 C l2 N H CrO 3 Cl PCC PCC 3. What carbonyl compound and phosphonium ylide pair is needed to synthesize the following compounds using the Wittig reaction? CH=CHCH 2 CH 2 CH 3 (a) (b) 4. 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 difference....
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