19.9(b)The 16-membered ring of 15-pentadecanolide is formed from 15-hydroxypentadecanoicacid.(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–oxygenbond of an alcohol remains intact when the alcohol reacts with a carboxylic acid to give anester.19.10Alkyl chlorides and bromides undergo nucleophilic substitution when treated with sodium iodide inacetone (Section 8.1). A reasonable approach is to brominate octadecanoic acid at its a-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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