Structure of Simpler Organic Compounds. 71 



namely, aldehydes, ketones, and the so-called fatty acids, 

 will be considered in detail later. The tertiary alcohols 

 give on oxidation a mixture of products, generally ketones 

 and acids, but the ketones obtained in this case contain a 

 smaller number of carbon atoms than the alcohol from 

 which they are derived. Thus, tertiary butyl alcohol, or 

 trimethyl carbinol, yields on oxidation a mixture of acetone, 

 CH 3 CO - CH, acetic acid, CH 3 - C0 2 H, or carbon dioxide 

 and other products. 



The above reactions are sufficient to determine only 

 whether any particular substance belongs to one of the three 

 classes that is, primary, secondary, or tertiary alcohols. 

 In the case of the butyl alcohols, which contain only four 

 carbon atoms, two isomerides which are primary alcohols, 

 and one secondary and one tertiary alcohol exist. If the 

 above- described oxidations were carried out on a butyl 

 alcohol of the formula C 5 H 10 O, it would be possible to 

 determine only whether such a substance were a primary, 

 secondary, or tertiary alcohol. If the result of these 

 experimental investigations indicated, for example, that the 

 substance was a primary alcohol, the question as to 

 whether it was butyl or isobutyl alcohol (formula (1) and 

 (2) ) would still remain undetermined. 



In the case of alcohols higher than butyl alcohol, a 

 still larger number of isomerides is capable of existence, 

 and the problem of the determination of the constitution 

 becomes still more complex. Thus, no less than eight 

 amyl alcohols of the formula C 6 H 12 can exist. 



The constitution of such substances can be finally 

 settled by a method which has rendered almost incal- 

 culable service to organic chemistry, namely, the method 

 of " synthesis," or the building up of complex from simpler 

 substances. 



A very good example of such a method is afforded by 



