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Unformatted text preview: O H (less stable cation) O H OH MAJOR (racemic) (single isomer) (single isomer) O R OH O O HO O Ph HO O H 2 SO 4 O I I Ph Cl OH O OTs O HO TA: Danny Ng 2/3/2003 Problem Set 4 (Chapter 11 Ethers) b) m-CPBA c) HI, heat 4. Synthesis. a} Draw the structures for the intermediates and final product. Pay attention to stereochemistry 1. NaNH 2 2. H 3 O, H 2 O + b) Provide the reagents to achieve the following transformation. O H O O Cl O O O Cl H H I O Ph H I O Ph H I H I O Ph H I H I O O O O O O O O HO Retro-synthesis: O HO HO H H HO HO I needs to be protected cis Forward HO O HO 1. H 2 SO 4 2. NaNH 2 3. 1-iodobutane (OH protection) 4. H 3 O + /H 2 O (OH deprotection) 5. H 2 /Lindlar’s cat. 6. m-CPBA...
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- Winter '05
- Chemistry, Ether, Alkyl, HO H HO H HO HO