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PS_9 - Br CH 3 SNa DMF 1 eq CCl 4 R-O-O-R(1 N Br O O 7 7...

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1 Problem Set #9 Swager 5.12 (Practice Only) 1. Rank the order of the following alkenes in terms of their electron density (1=most electron rich, 4=most electron poor). Which one will react fastest with HBr? Explain your reasoning. 2. Provide reagents (with mechanisms) to carry out the following reactions. CH 3 CH 3 CH 3 CH 3 OH Br OH Br + Enantiomer + Enantiomer H 3 CO H 3 CO
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2 OH OH OH
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3 3. Propose curved arrow mechanisms. OH O Br Br 2 , H 2 O
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4 4. Rank the following series of molecules reactivity for the indicated processes. Place the rank in the box given (1=Fastest). Reaction with methylbromide CH 3 ONa CH 3 CH 2 ONa (CH 3 ) 3 CONa (CH 3 ) 3 COH
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5 5. Suggest reagents to best carry out the following transformation. Shown all intermediates.
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6 6. Give the product(s) for each of the following reactions. Show stereochemistry where appropriate. OH Br TsOH, CH 3 OH, ! CH 3 I Et H H (CH 3 ) 3 COK, THF
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Unformatted text preview: Br CH 3 SNa, DMF 1 eq. CCl 4, R-O-O-R (1%), ! N Br O O 7 7. Predict the major product of each of the following S N 2 reactions. If you do not expect a reaction to occur, then write "NR". Be sure to indicate stereochemistry. Br I I H 3 C H 3 C CH 3 Cl CH 3 Cl Br H N H 3 C CH 3 CH 3 NaH (NaH acts as a base) NaN 3 DMF 1. eq. KCN acetone NaOMe DMF 8 8. More than one product is formed in each of the following substitution reactions. Provide the products and the mechanisms for their formation. OTf H 3 C CH 3 H 3 C CH 3 Br MeOH, ! EtNH 2 , ! 9 9. Provide a detailed mechanism for the following reactions. HBr CH 2 Cl 2 Br H 2 SO 4 (trace water) 10 10. Give the product and all intermediates to the following reaction sequence. OH 1. NaH, THF 2. 3. H + /H 2 O 4. POCl 3 + Pyridine O...
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