222-11 OYO#5

222-11 OYO#5 - 1 Chem 222 OYO#5 1 Provide four synthetic...

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1 Chem 222 OYO#5 3/2/11 1. Provide four synthetic steps for the following conversion: CH 3 (also ortho methyl) Br (±) 2. Ehren D. in (222-2010; 9:35 section) wondered about the possibility of epoxide formation during the Wittig reaction. Provide a complete arrow-formalism mechanism for this conversion. O H 2 C PPh 3 epoxide There is no epoxide formation with the phosphonium ylide, but it is possible to isolate the epoxide product by using a sulfur ylide, H 2 CS(Me) 2 via the same mechanism you have drawn above. Why do you think there is a change in reactivity for the sulfur vs. the phosphonium ylide? On Friday ( 3/3/11 ), we will learn more about α , β -unsaturated carbonyl compounds. After Friday’s lecture , explain the difference in reactivity below. Be sure to include the correct arrow-formalism for each conversion. O (H 3 C) 2 HS O CH 2 O + DMSO O (H 3 C) 2 S CH 2 O 3. Provide the correct arrow-formalism for the following iodolactonization reaction. Recall how halogens
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222-11 OYO#5 - 1 Chem 222 OYO#5 1 Provide four synthetic...

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