Dolbier HW Solutions 475

Dolbier HW Solutions 475 - 569 CARBOXYLIC ACID DERIVATIVES:...

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20.39 ( a ) The rearrangement in this problem is an acyl transfer from nitrogen to oxygen. This rearrangement takes place in the indicated direction because it is carried out in acid solution. The amino group is protonated in acid and is no longer nucleophilic. ( b ) The trans stereoisomer of compound A does not undergo rearrangement because when the oxygen and nitrogen atoms on the f ve-membered ring are trans, the necessary tetrahedral intermediate cannot form. 20.40 The ester functions of a polymer such as poly(vinyl acetate) are just like ester functions of simple molecules; they can be cleaved by hydrolysis under either acidic or basic conditions. To prepare poly(vinyl alcohol), therefore, polymerize vinyl acetate to poly(vinyl acetate), and then cleave the ester groups by hydrolysis. 20.41 ( a ) Each propagation step involves addition of the free-radical species to the b -carbon of a mole-
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