Dolbier HW Solutions 454

Dolbier HW Solutions 454 - 548 CARBOXYLIC ACID DERIVATIVES:...

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20.20 Step 1: Nucleophilic addition of hydroxide ion to the carbonyl group Step 2: Proton transfer to give neutral form of tetrahedral intermediate Step 3: Proton transfer from water to nitrogen of tetrahedral intermediate Step 4: Dissociation of N -protonated form of tetrahedral intermediate Step 5: Irreversible formation of formate ion 20.21 A synthetic scheme becomes apparent when we recognize that a primary amine may be obtained by Hofmann rearrangement of the primary amide having one more carbon in its acyl group. This amide may, in turn, be prepared from the corresponding carboxylic acid. CH 3 CH 2 CH 2 NH 2 CH 3 CH 2 CH 2 CO 2 H CH 3 CH 2 CH 2 CNH 2 O 1 1 Water HOH OH 2 Hydroxide ion Formic acid O HC OH Formate ion O
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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