PS_8 - mechanism each product is produced. H 3 C O OTs Br I...

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1 Problem Set #8 Swager 5.12 (Due Thursday , November 10, 2011 at 4PM) 1. Give the major substitution product(s) of the following reactions. Indicate which of the major products will be dominant. If no reaction will occur then indicate by writing NR and give a very brief explanation. Show stereochemistry when important. Br CH 3 CH 2 CH 2 OH, ! CH 3 N CH 3 S - NaCN Cl NaI, acetone CH 3 Br CH 3
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2 2. Give the major product(s) of the following reactions. If no reaction will occur then indicate by writing NR. Show stereochemistry when important. I Br ! Br 0.5 eq. S 2- MeONa Br (CH 3 ) 3 COK CH 3 HN(CH(CH 3 ) 2 ) 2 Br 2
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3 3. For the following compounds, designate whether they will react under S N 1 conditions (e.g., EtOH, Δ ), S N 2 conditions (KI/acetone), both, or neither. Indicate the products and by which
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Unformatted text preview: mechanism each product is produced. H 3 C O OTs Br I Br Br H 3 C O Br Br 4. Solvolysis of this compound (enantiomerically pure) produces 2 isomeric compounds. Identify these compounds. I H 3 C EtOH ! Bu Bu= Butyl C 13 H 28 O 4 5. The following rearrangement occurs very readily in high yield with acid catalysis. Provide a mechanism and a brief explanation for this very selective process. HO OH O H + + H 2 O 6. When alkyl halides are treated with aqueous silver nitrate, silver halide precipitates and an alcohol is formed. Propose a mechanism for the following reaction. I OH Ag + H 2 O 5 7. Suggest detailed curved arrow mechanisms for the following reaction. I OEt CH 3 CH 3 H 3 C H 3 C EtOH, ! + HI...
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PS_8 - mechanism each product is produced. H 3 C O OTs Br I...

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