594 THE GRIGNARD SYNTHESIS : THE ACTION OF 



duct decomposed with water, that secondary and tertiary 

 iilcohols are formed respectively, the reactions taking phxce ia 

 iiccordance with these equations : — 



I. /OMgX 



R'MgX + RCHO -- RCH< 



\R' 



/OMgX /OH 



RGB < +H0O = RC\ +Mg;OH).wHX 



\R' ' \R' 



II. /OMgX 



R'MgX + R-CO-R" = RC<rR" 

 \R' 

 xOMgX Rx /OH 



RC^H," +H0O = ^C'' +Mg(OH)., + HX 



\R' R'/ \R" 



In these reactions the double linking of the oxygen of the 

 aldehyde or ketone is broken, and one of the free bonds of the 

 oxygen unites with hydrogen to form hydroxy 1, while the free 

 carbon bond takes up a hydrocarbon residue. 



Japan camphor CjoHi,;0 contains the ketone group C=0 ; 

 under the influence of an organo-magnesium compound, it should 

 therefore form a tertiary alcohol. Zeli'nsky,^ who has done a 

 great deal of work on the preparation of cyclic alcohols, found 

 that when camphor is treated with magnesium methyl iodide, 

 and the reaction product decomposed with water, there is 

 obtained a tertiary alcohol whose composition is expressed by 

 the formula CiiH.,|0.' 



'No work having been done on the action of organo- 

 magnesium halides of the aromatic series on ketones, it was 

 decided to investigate the action of magiiesiumphenylbromide 

 on Japan camphor. 



Expei'imenial. 



32 g. of phenyl bromide dissolved in 1^ times its weight of 

 ether, was allowed to drop slowly oa the calculated amount, 



1 Ber. d deut. chem. Ges , 1901, .34, 2877. 



2 Ibid. 



