Ch_322b_18.11

Ch_322b_18.11 - Chapter 18.11 lecture note

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Carboxylic Acid Anhydrides Synthesis Acid anhydrides of acyclic carboxylic acids are difficult to prepare directly by dehydration because of the exothermicity of the reverse hydrolysis reaction. R-C-O-C-R O = O anhydride + H 2 O 2 RCOH O + energy higher energy lower energy
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In biological systems, phosphoric acid anhydrides are used to store and release energy: N N NH 2 N N O OH HO H H H H CH 2 -O-P-O-P-O-P-O adenine ribose O = O O O - O - O - - adenosine triphosphate (ATP) + H 2 O CH 2 -O-P-O-P-O-H O O O O - O - O - - + HO-P-O adenosine diphosphate (ADP) Approximately 9 kcal of energy are released per mole of ATP hydrolyzed. Chemical energy from oxidation reactions promotes conversion of ADP to ATP.
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Preparation of Acid Anhydrides Only acetic anhydride , among the aliphatic acid anhydrides, is commercially available. It is prepared on large scale by the high temperature dehydration of acetic acid to ketene . CH
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Ch_322b_18.11 - Chapter 18.11 lecture note

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