Chem634_F11_PS02 - Chemistry 634 Advanced Organic Chemistry...

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Chemistry 634: Advanced Organic Chemistry – Synthesis and Reactivity Fall 2011, University of Delaware Prof. Donald Watson Problem Set 2 Due Beginning of Class 9/20/10 You may work in groups, unless otherwise noted. No not try to fit answers on these pages, use separate paper. 1) Order the following sets (1 being greatest) and explain why: a) Most electrophilic O NMe 2 Bu O OMe Bu O Cl Bu b) Most sterically crowded amine Me Me Me Me Me Me H 2 N NH 2 Me Me Me NH 2 Me Me NH 2 c) Most acidic (H 2 O), provide pKa’s for each O OH Me 2 N O OH F 3 C O OH d) Most acidic (DMSO), provide pKa’s for each O NBu 2 Me O OBu Me O Bu Me H H H e) Longest expected C=O bond length. O NMe 2 Bu O OMe Bu O Cl Bu 2) Predict the products of the following reactions and provide a complete mechanism: Me OH 1) TsCl, pyr 2) NaI, Acetone Me Me SOCl 2 , pry then NaCN NH 2 O HO Et P(O)Cl 3 Et 3 N N EMO Me HO H SOCl 2 , py OH Me OH O P PhO PhO N 3 N N (DBU) HO O Me Me Me OH OBn PPh 3 DEAD
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3) Provide a mechanism for the following reactions. Be detailed (obey 3-arrow rule).
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Chem634_F11_PS02 - Chemistry 634 Advanced Organic Chemistry...

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