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 specifies 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 oxygenCH3CONHC6H5AcetanilideHOHHHydronium ionCH3CNC6H5HOHProtonated formof amideOHHWaterheatCNH2OOCONH4Ammonium phthalamateOOPhthalimide
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