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Dolbier HW Solutions 652 - 746 LIPIDS(e The carbon chain...

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( e ) The carbon chain must be shortened by one carbon atom in this problem. A Hofmann rearrange- ment (text Section 20.17) is indicated. ( f ) Lithium aluminum hydride reduction of octadecanamide gives the corresponding amine. ( g ) Chain extension can be achieved via cyanide displacement of bromine from 1-bromoocta- decane. Reduction of the cyano group completes the synthesis. 26.23 First acylate the free hydroxyl group with an acyl chloride. Treatment with aqueous acid brings about hydrolysis of the acetal function. The two hydroxyl groups of the resulting diol are then esteri fi ed with 2 moles of the second acyl chloride. 26.24 The overall transformation to OH SCH 3 HOCH 2 CHCH
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