Selected_Problems_Polymer - Chem 358 Spring 2006...

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Chem 358 Spring 2006 Application to Polymer Synthesis 1. Write down the structure of the polymer you would expect to form in each of the following reactions. The structure containing one or two repeat units is sufficient. O O O + Acid catalyst Heat HOCH 2 CH 2 CH 2 OH (a) H 2 N NH 2 CH 3 O O O OCH 3 Heat (b) 150°C O (c) A B A B n moles (Excess) Benzene (CH 3 ) 3 C - Li + Ph Ph (Benzoyl peroxide) (d) Intramolecular reaction Ph O O Ph O O THF, F O CH 3 O O CH 3 O (e) CH 3 CH 3 CH 3 O O (CH 3 ) 3 Si 2. Based on your knowledge of the reactions of anhydrides with amines and other nucleophiles (Louden Chapter 21) suggest a plausible mechanism for the formation of the polymer shown from the amino anhydride shown below. O CH 2 -NH 2 O O N O CH 2 O CH 2 N O O N O O CH 2 ! 125 °C
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3. Based on your knowledge of the Hammond’s postulate explain mechanistically the formation of the observed polymer. Give reasons as to why the expected polymer does not form. CH
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Selected_Problems_Polymer - Chem 358 Spring 2006...

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