20.16Methanol 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 suitablenucleophiles. The nucleophile in this case is methylamine.(c)The acyl group is . Because the problem specifes that the acyl transfer agent is amethyl ester, methyl formate is one of the starting materials.20.18Phthalic anhydride reacts with excess ammonia to give the ammonium salt of a compound knownas phthalamic acid.Phthalimide is formed when ammonium phthalamate is heated.20.19Step 1: Protonation of the carbonyl oxygen11CH3CONHC6H5AcetanilideHOHH1Hydronium ionCH3CNC6H5HOH1Protonated formof amideOHHWaterheatCNH2OOCO2 NH4Ammonium phthalamateOOPhthalimide
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