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Dolbier HW Solutions 452 - 546 CARBOXYLIC ACID DERIVATIVES...

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20.16 Methanol is the nucleophile that adds to the carbonyl group of the thioester. 20.17 ( b ) Acetic anhydride is the anhydride that must be used; it transfers an acetyl group to suitable nucleophiles. The nucleophile in this case is methylamine. ( c ) The acyl group is . Because the problem speci fi es that the acyl transfer agent is a methyl ester, methyl formate is one of the starting materials. 20.18 Phthalic anhydride reacts with excess ammonia to give the ammonium salt of a compound known as phthalamic acid. Phthalimide is formed when ammonium phthalamate is heated. 20.19 Step 1: Protonation of the carbonyl oxygen CH 3 C O NHC 6 H 5 Acetanilide H O H H Hydronium ion CH 3 C NC 6 H 5 H OH Protonated form of amide O H H Water heat CNH 2 O O CO NH 4 Ammonium phthalamate O O Phthalimide
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