Dolbier HW Solutions 449

Dolbier HW Solutions 449 - 543 CARBOXYLIC ACID DERIVATIVES:...

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20.9 The starting material contains three acetate ester functions. All three undergo hydrolysis in aqueous sulfuric acid. The product is 1,2,5-pentanetriol. Also formed in the hydrolysis of the starting triacetate are three molecules of acetic acid. 20.10 Step 1: Protonation of the carbonyl oxygen Step 2: Nucleophilic addition of water Step 3: Deprotonation of oxonium ion to give neutral form of tetrahedral intermediate Step 4: Protonation of ethoxy oxygen 1 Oxonium ion C 6 H 5 C OCH 2 CH 3 OH HO H 1 O H H Water 1 C 6 H 5 C OCH 2 CH 3 OH HO Tetrahedral intermediate O H H H 1 Hydronium ion 1 O H H 1 C 6 H 5 C OCH 2 CH 3 OH O 1 H H C 6 H 5 C OCH 2 CH 3 OH
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