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Unformatted text preview: Chem 3580 - Spring 2009 Combined Problem Set 13 - Solution Application to Polymer Synthesis Challenging Problems 1. O O O + Acid catalyst Heat HOCH 2 CH 2 CH 2 OH (a) HO CH 2 CH 2 CH 2 O O O OCH 2 CH 2 CH 2 O O O OH (i) This is AA + BB (ii) A= OH, B= COOH (anhydride is a masked diacid diacid in disguise). It does not matter which one you designate as A and which one as B. It is arbitrary. (iii) Nucleophilic acyl substitution between an alcohol and an anhydride to form an ester and direct acid-catalyzed esterification (Fischer esterification). H 2 N NH 2 CH 3 O O O OCH 3 Heat (b) 150C Here two repeat units are written. The brackets show two of the possible ways of grouping the repeat units. N N N N H H O O H H O O N N N N H H O O H H O O O (c) A B n moles (Excess) Benzene (CH 3 ) 3 C- Li + A B n-1 Li n-1 OH Ph Ph (Benzoyl peroxide) (d) Intramolecular reaction Ph O O Ph O O Diene This question illustrates the following: (1) When two intermediates are possible, the more stable one predominates...
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