Dolbier HW Solutions 447

Dolbier HW Solutions 447 - phthalic anhydride Phthalic...

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( c ) The reaction of phthalic anhydride with dimethylamine is analogous to that of part ( b ). The organic products are an amide and the carboxylate salt of an amine. In this case both the amide function and the ammonium carboxylate salt are incorporated into the same molecule. ( d ) The disodium salt of phthalic acid is the product of hydrolysis of phthalic acid in excess sodium hydroxide. 20.8 ( b ) The tetrahedral intermediate is formed by nucleophilic addition of ammonia to one of the car- bonyl groups of acetic anhydride. Dissociation of the tetrahedral intermediate occurs by loss of acetate as the leaving group. ( c ) Dimethylamine is the nucleophile; it adds to one of the two equivalent carbonyl groups of
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Unformatted text preview: phthalic anhydride. Phthalic anhydride Dimethylamine 1 Tetrahedral intermediate HN(CH 3 ) 2 O HO N(CH 3 ) 2 O O O O Acetamide Ammonium acetate Ammonia 1 tetrahedral intermediate CH 3 CNH 2 O 1 H 4 N 2 OCCH 3 O 1 O H CH 3 C OCCH 3 O NH 2 H 3 N Tetrahedral intermediate NH 3 O CH 3 COCCH 3 O CH 3 COCCH 3 NH 2 O HO 1 2NaOH Sodium hydroxide Phthalic anhydride O 1 H 2 O Water Sodium phthalate CO 2 Na 1 CO 2 Na 1 O O O O 1 2(CH 3 ) 2 NH Dimethylamine Phthalic anhydride O H 2 N(CH 3 ) 2 1 Product is an amine salt and contains an amide function. CO 2 CN(CH 3 ) 2 O O O O O CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 541...
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