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Dolbier HW Solutions 517

Dolbier HW Solutions 517 - This suggests the sequence HNO 3...

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The preferred order of proton removal in Hofmann elimination reactions is b CH 3 . b CH 2 . b CH. Ethylene is the major alkene formed, the observed ratio of ethylene to 1-butene being 98 : 2. 22.14 ( b ) The pattern of substituents in 2,4-dinitroaniline suggests that they can be introduced by dini- tration. Since nitration of aniline itself is not practical, the amino group must be protected by conversion to its N -acetyl derivative. Hydrolysis of the amide bond in 2,4-dinitroacetanilide furnishes the desired 2,4-dinitroaniline. ( c ) Retrosynthetically, p -aminoacetanilide may be derived from p -nitroacetanilide.
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Unformatted text preview: This suggests the sequence HNO 3 H 2 SO 4 CH 3 CNH O Acetanilide H 2 N Aniline 1. Fe, HCl; 2. HO 2 or 1. Sn, HCl; 2. HO 2 or H 2 , Pt CH 3 CNH NO 2 O p-Nitroacetanilide (separate from ortho isomer) CH 3 CNH NH 2 O p-Aminoacetanilide CH 3 COCCH 3 O O CH 3 CNH O NH 2 p-Aminoacetanilide CH 3 CNH O NO 2 p-Nitroacetanilide 2,4-Dinitroaniline NH 2 NO 2 NO 2 2,4-Dinitroacetanilide NHCCH 3 NO 2 NO 2 O H 2 O, HO 2 , or 1. H 2 O, H 1 2. HO 2 NH 2 Aniline Acetanilide NHCCH 3 O 2,4-Dinitroacetanilide NHCCH 3 NO 2 NO 2 O HNO 3 H 2 SO 4 CH 3 CCl O or CH 3 COCCH 3 O O AMINES 611...
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