Question

3. The bacteriostatic drug sulfanilamide, which predates penicillin, used to be prepared from acetanilide in several steps. a) Suggest a synthesis. In contrast to most synthetic problems, this one will require you to make comparisons between functional groups and suggest extension of chemistry you've seen to new contexts. b) Why do you think acetanilide was used as a starting material rather than aniline? O=$=0 NH2

Answer 1

Retae ynthesix NH NH Ct +NH3 NH NH NH toH ct ct t not C.I Sythesi: S tkenit cannet electrephile itselp generate an 1

take chloso sulphonic acid Sa 6ニSニ。 2-5-0-H/ as-cr Elechrop hile

NH-S NH H-N-SIC I1 -C) ThA iA unewanted pa-duct Aniline CA Ae So e we as it 1it ill seact t7ke this unwank above. to avoid seaction have to pootedt lone Cue H deactivating it pai s of houdd yarcly! group. So ue Aretanilide bu not Aniline use HN E C NH

S0 synthesix i di'y initia ted Aretani i de available PH-2-CH NH- CH EAN 2-CH3 Q HN -C NH2 NH2 HCT/H -NH2