MT3_Wi05 - NU Chem 210-2, Winter 2005 MT 3 2 1. (20 pts)...

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NU Chem 210-2, Winter 2005 MT 3 2 1. (20 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) O O OEt 1) TsOH, Dean-Stark conditions Ethylene glycol 2) LiAlH 4 3) H 2 O, H 3 O + heat b) c) O O O 2 d) TsOH catalyst Dean-Stark, heat OH O OH e) 1. HCCH, NaNH 2 2. H 3 O + work up 3. H 2 , Lindlar’s catalyst 4. H 2 SO 4 conc. O
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NU Chem 210-2, Winter 2005 MT 3 3 2. (20 pts) Propose a curved arrow mechanism for the following reaction. Show all the proton transfer steps. N OH HCl, HOC(O)CH 3 O N H
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NU Chem 210-2, Winter 2005 MT 3 4 3) (20 pts) The following reaction proceed nicely with very mild heat. Propose a curved arrow mechanism for it showing all the proton transfer steps. Provide the possible reason(s) for this reaction not needing a Lewis-acid or a Bronsted-acid activation. Provide the possible reason(s) for this reaction not needing a drying agent or the Dean-Stark procedure. Hint:
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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MT3_Wi05 - NU Chem 210-2, Winter 2005 MT 3 2 1. (20 pts)...

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