Dolbier HW Solutions 451

Dolbier HW Solutions 451 - 545 CARBOXYLIC ACID DERIVATIVES...

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20.13 Because ester hydrolysis in base proceeds by acyl oxygen cleavage, the 18 O label becomes incorporated into acetate ion . 20.14 Step 1: Nucleophilic addition of hydroxide ion to the carbonyl group Step 2: Proton transfer from water to give neutral form of tetrahedral intermediate Step 3: Dissociation of tetrahedral intermediate Step 4: Proton transfer from benzoic acid 20.15 The starting material is a lactone, a cyclic ester. The ester function is converted to an amide by nucleophilic acyl substitution. Methylamine 4-Pentanolide 4-Hydroxy- N -methylpentanamide 1 CH 3 NH 2 O CH 3 O CH 3 NHCCH 2 CH 2 CHCH 3 OH O Benzoic acid Hydroxide ion O C 6 H 5 C OH 1 Water Benzoate ion 2 C 6 H 5 C O 1 HO 2 11 1 Tetrahedral intermediate
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