s20 2011 week 3 day 4

s20 2011 week 3 day 4 - Chemistry S-20ab Week 3 Chemistry...

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Synthesis of Epoxides With Halohydrins Provide complete curved-arrow mechanisms for each step in the following transformation. Be sure to pay attention to stereochemistry! Br 2 , H 2 O OH Br (+/–) NaOH O (+/–) Explain why the following halohydrin cannot be transformed into an epoxide: OH Br Reading : Section 11.2 Chemistry S-20ab Week 3 1 ±²
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Synthesis of Epoxides With Peroxycarboxylic Acids A much more convenient, one-step synthesis of epoxides from alkenes uses peroxycarboxylic acids, often called “peracids.” Some examples: R O O O H O O H O Cl a general peracid mCPBA meta -chloroperoxybenzoic acid Draw the curved arrows for the following single-step synthesis of an epoxide from an alkene: O O O O H R O O H R Identify the molecular orbitals involved in this reaction. Is this mechanism similar to any other reactions you have seen before? Reading : Section 11.2 Chemistry S-20ab Week 3 1 ±²
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Opening Epoxides: Acidic Conditions Provide a mechanism and explain why the indicated product is formed selectively in each of the following reactions: O (+/–) mCPBA CH 3 OH H + OH O CH 3 (+/–) Reading : Section 11.4 Chemistry S-20ab Week 3 1 ±²
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Opening Epoxides: Basic Conditions Provide a mechanism and explain why the indicated product is formed selectively in each of the following reactions: O (+/–) mCPBA OH (+/–) NaOCH 3 O CH 3 Reading : Section 11.4 Chemistry S-20ab Week 3 1 ±²
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s20 2011 week 3 day 4 - Chemistry S-20ab Week 3 Chemistry...

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