Dolbier HW Solutions 412 - 506 CARBOXYLIC ACIDS 19.9(b The...

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19.9 ( b ) The 16-membered ring of 15-pentadecanolide is formed from 15-hydroxypentadecanoic acid. ( c ) Vernolepin has two lactone rings, which can be related to two hydroxy acid combinations. Be sure to keep the relative stereochemistry unchanged. Remember, the carbon oxygen bond of an alcohol remains intact when the alcohol reacts with a carboxylic acid to give an ester. 19.10 Alkyl chlorides and bromides undergo nucleophilic substitution when treated with sodium iodide in acetone (Section 8.1). Areasonable approach is to brominate octadecanoic acid at its -carbon atom, then replace the bromine substituent with iodine by nucleophilic substitution. 19.11 ( b ) The starting material is a derivative of malonic acid. It undergoes ef
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