Dolbier HW Solutions 412

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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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). 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
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.
Ask a homework question - tutors are online