326 



VII. ACIDS, AMIDES, ALDEHYDES AND HYDROCARBONS 



(1) Primary alcohols are formed by the reduction of the corresponding 

 fatty acids. 



(2) Paraffins, secondary alcohols, and ketones originate by indirect 

 decarboxylation of the corresponding (n + 1) acids. 



(3) Saturated acids, ketonic acids, and hydroxy-acid soriginate by syn- 

 thesis from shorter intermediates. 



-CO2 

 CH3-(CH2)36-COOH > CH3(CH2)s5CH3 



-20 



+ H2 



-^ CH3(CH2)34-CH20H 



CH3-(CH2)34-COOH - 



-20 -COf CH3-(CH2)33-CH3 



CH3(CH2)32-COOH 



CH3(CH2)24-COOH 



CH3(CH2)22COOH 



+ H2 



-> CH3(CH2)32CH20H 



-CO2 CH3(CH2)3lCH3 



+H2 



-> CH3(CH2)24-CH20H 



-OO2 CH3(CH2)23-CH3 



+H2 



^ CH3(CH2)22CH20H 



Fig. 1. The origin of the primary alcohols and hydrocarbons by reduction of fatty 

 acids or by their decarboxylation according to Chibnall and Piper.'" 



CH3-(CH2)32-COOH 

 n-Tetratriacontanoic acid 



General synthesis 



CH3 • (CH2)n • CH : CH : (CH2),3 • COOH 

 + 

 CH3 • (CH2)i8 • CO • (CH2),3 • COOH 

 + H2 



CH3 • (CH2),8 • CO • (CH2)l3 ■ CH2OH 



Cocceryl alcohol 

 Fig. 2. Suggested origin of cocceryl alcohol in waxes. i" 



