sol_05 - Garbage Problem Set #5, 5.12 Spring 2003 Due...

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Unformatted text preview: Garbage Problem Set #5, 5.12 Spring 2003 Due Monday, March 31, 4pm 1. a) Rank the following series of molecules based on reactivity in an 8N2 reaction (Nal/acetone). (1 = fastest 3N2, 4= slowest 3N2) Me Me Me Me Me Me Me Me >40] M29 Mew Me MeMOTf Cl Br [H b) Rank the following series of molecules based on reactivity in an 8N1 reaction (EtOH/heat). (1= fastest 8N1, 4= slowest 5N1) Br Me\/k M Me Br MeM Me Me Me W E] c) Rank the following series of molecules based on reactivity in an E2 reaction (NaO’Pr/ ’PrOH). (1 = fastest E2, 4: slowest E2) Um O’Br MeUBr O/Br tBu "”Me iPr‘" 2. a) Predict the product of the following reaction, and provide the mechanism for its formation. it Z Br Me K+ -6tBu \ M WW tBuOH i l X N (E13 V N H H4 H b) Draw a picture of the transition state for the above reaction. Pay attention to stereochemistry! \\\ $13th c) If the same molecule were heated in diisopropylamine (’PrgNH), would you expect the same productthatyou drewin parta? Whyorwhynot? Nol ~11“ rQKvH 0H— A R db} M (W N am l eQA‘me. aw El eQAeranM Wm 0k "flown: WWW, balk Aiken? 180m cam APMl‘m in gmamo/ % M+ g—leo lWKW/{l’M‘WMEl H R fir ’HQ \-l (kg; 8 \ j”) + H vg/ W a) H A PO )Yr N M 3. Predict the products of the following substitution reactions, and specify whether each proceeds by SN1 or 8N2. Pay attention to stereochemistry. b) QM an: ; Me on KCN M MeAXMe DMF o) F F CI Nal § acetone, A ( / SM J 4. The reaction conditions are very important in determining what products are obtained in elimination reactions. Predict the major products of the following elimination reactions. Br :Me Li+ ‘N’Pr2 -‘ Na+ ‘NH2 “my b “le” Z I gr Na+-0Me Me = MeNH2,A \ - (NON AHA) QED \li/l r1 Br EtsN, A Me Na+ _OMe \ \ E I r " / C > SM W6 5. (Bromomethyl)cyclohexane undergoes the following two reactions: CH3 A Br OEt (1) EtOH Cm a) Provide a detailed mechanism for reaction (1). gm ! “A?” c) Draw reaction-energy diagrams for the reactions on the previous page. Clearly label starting materials, intermediates, products, and the rate-determining step for each reaction. Reaction (1) > 9’ (D C LIJ Reaction Coordinate Reaction (2) > 9 (D C Lu Reaction Coordinate 6. The mechanism of the following reaction involves mechanistic steps that you are already familiar with. Provide a detailed mechanism. M H+ ll “ tug/H $1335: :2 :2 Q ...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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sol_05 - Garbage Problem Set #5, 5.12 Spring 2003 Due...

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