Weekly Review 4 (Key)

Weekly Review 4 (Key) - Review4 ChemS20ab 1 Sodium ethoxide...

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Review 4 Weekly Review Lecture Answers Chem S 20ab 1. Sodium ethoxide will substitute for chloride in one of the substrates below but shows no reaction with the other, similar substrate. The anionic intermediate is too unstable for the molecule on the right. Therefore, this reaction has too high an activation energy.
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Review 4 Weekly Review Lecture Answers Chem S 20ab 2. Provide a complete curved arrow mechanism for the following transformation: OO CHO H 2 O, H + O O O H CHO CHO O OH H 2 O CHO H 2 O O OH CHO HO HO OH H + transfer H OH O H + transfer H O OH HO OH H O HO OH H O O OH 2 H + transfer HO HO H O O OH O O O H Sol
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Review 4 Weekly Review Lecture Answers Chem S 20ab 3. Provide a mechanism and predict the product: HO MeO 1) H + 2) Br 2 ,FeBr 3 H + H 2 O MeO MeO MeO H Sol MeO MeO FeBr 3 Br Br Br Br FeBr 3 Br H Sol MeO Br Note: The –SH group replaces only the indicated Br, because this is the only position that allows the anionic intermediate to be stabilized by the strongly electron-withdrawing nitro group.
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This note was uploaded on 01/22/2012 for the course CHEM CHEM E-2B taught by Professor Loganmccarty during the Summer '09 term at Harvard.

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Weekly Review 4 (Key) - Review4 ChemS20ab 1 Sodium ethoxide...

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