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Unformatted text preview: unless the substrate is an acyl chloride (Cl- leaving group is too weakly basic to get protonated) ..... Under base/neutral conditions, the leaving will always leave without prior protonation unless the substrate is an amide (the amine leaving group of an amide will get protonated before it departs). CH 3 C O Cl + O-CH 3 .. .. : C O O-CH 3 .. .. + Cl-CH 3 C O O-CH 3 .. .. + H 2 O H + heat CH 3 C O O-CH 3 .. .. + OH-heat .. : H 2 O .. : CH 3 C O NH 2 CH 3 C O OH + HOCH 3 CH 3 C O OH + HOCH 3 Note: will be present as CH 3 C O O because of basic conditions + OH-heat H 2 O .. : CH 3 C O OH + NH 3 A. B. C. D....
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