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Problem_Set_13

Problem_Set_13 - Chem 3580 Spring 2009 Combined Problem Set...

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Chem 3580 - Spring 2009 Combined Problem Set 13 Application to Polymer Synthesis – Challenging Problems Some of these will be done during the Friday session. Not all reactions here have been used in class to form polymers. 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) (i) Type of reaction: AA + BB or AB? Write down the A and the B functional groups. (ii) (iii) What is (are) the underlying basic organic reaction(s)? H 2 N NH 2 CH 3 O O O OCH 3 Heat (b) 150°C O (c) A B n moles (Excess) Benzene (CH 3 ) 3 C - Li + Ph Ph (Benzoyl peroxide) (d) Intramolecular reaction Ph O O Ph O O 2. Based on your knowledge of the reactions of anhydrides with amines and other nucleophiles (Chapter 16) suggest a plausible mechanism for the formation of the polymer shown from the amino anhydride shown below. (Hint: imide formation from anhydrides)
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Problem_Set_13 - Chem 3580 Spring 2009 Combined Problem Set...

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