CHM 151 (PS 9 KEY F07)

CHM 151 (PS 9 KEY F07) - CHEMISTRY 151L.001 Fall 2007...

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CHEMISTRY 151L.001 Fall 2007 Problem Set 7 1. Considering the following table and what you know about the unimolecular and bimolecular substitution and elimination mechanisms predict the products of the following reactions and pay attention to stereochemistry: STRONG BASES WEAK BASES GOOD NUCELOPHILES HO , RO RC C I - , Br - , RS - , CN - , N 3 - POOR NUCLEOPHILES (CH 3 ) 3 CO ( t -BuOK) , other bulky alkoxides Cl - , F - , RCO 2 , H 2 O, ROH, PR 3 , OTs NaOH OTs NaO t- Bu OTs H 2 O HOH HO Bu OH OH S N 2 + E2 E2 OH SN1/E1 Ph Br NaCN HOCH 3 Ph CN What are two ways you could speed this reaction up – but get the SAME product? Cl NaI H 3 C C O CH 3 I major (from SN2) How could you increase rate of this reaction and still get the same product? OCH 3 CH 3 OH Br OCH 3 SN1/E1
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CHM 151L.001; Problem Set 7 2 Br NaN 3 DMSO N 3 (S N 2) Cl NaOH HOH, heat major OMs O O DMSO No reaction or SLOW reaction to form substitution product. How could you promote the SN1 mechanism? 2 halide (open to any mech, some branching slows SN2), poor nucleophile (favors uni – SN1/E1),
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CHM 151 (PS 9 KEY F07) - CHEMISTRY 151L.001 Fall 2007...

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