Structure of Simpler Organic Compounds. 1 1 5 



CH.,Br CH 2 CN 



I + 2KCN = | 

 CH 2 Br CH 2 CN 



CH 2 CN CH 2 -COOH 



+ 4H 2 = | + 2NH 3 



CH 2 CN CH 2 COOH 



It yields an anhydride of the formula 



CH 2 .(XX 

 I > 



CH,/ 



[ 2 -CO 



Adipic acid, COOH (CH 2 ) 4 COOH, is obtained by 

 heating fats with nitric acid (hence the name). 



SUMMARY. The dicarboxylic acids contain two car- 

 boxyl groups, and act as dibasic acids. The chief members 

 of the series of interest are oxalic, malonic, and succinic 

 acids. The ester of malonic acid, CH^GOOCgH^, yields 

 a sodium compound, CHNa(CO - OG S H 5 ) S , which reacts 

 with alkyl halogen compounds to form alkyl substituted 

 malonic esters, CHR(CO - OC 2 H 5 ) 2 , from which, by a series 

 of reactions, alkyl substituted acetic acids can be formed 

 of the general formula CH 2 R COOH. From the alkyl 

 mcdonic esters, sodium compounds, CNaR(CO OC g H 5 ) s , can 

 be obtained, which with alkyl iodides yield derivatives of 

 the type CRR'(CO OC 2 H 5 ) S , from which dialkyl substituted 

 acetic acid derivatives, CHRR' - CO OH, can be formed. 



Each of the carboxyl groups in the dibasic acids can 

 undergo the ordinary reactions characteristic of this 

 group. 



Part X. The Hydroxy Acids. 



Amongst the oxidation products of ethylene glycol, 

 mention has been already made of glycollic acid 



CH 2 OH 



COOH 



