Adipic Acid Adipic acid (or 1,6-Hexanedioic Acid) is an important intermediate in the synthesis of nylon [6-6]. It’s an important bifunctional molecule. Adipie acid is obtained by the oxidative cleavage of eyelohexanone with KMnOy. KMnh0x is a very powerful oxidant. It is the most powerful oxidant in this lab (it’s even more powerful than Jones reagent). The mechanism of this process is believed to involve the cleavage of an enolic intermediate (see Advanced Organic Chemistry 2" Edition, Part B pp. 517 by Carey, JACS 87, 5202 (1965), JACS 89, 6691 (1967)) In aketone the keto form is highly favored over the eno] form. However, acid or base can catalyze the formation of the enol: ° ° ¢ ¥ ° 4 a i On = fe e 4 + %e K bee oH on | H — ne — — a a ‘The progress of the reaction is monitored by the disappearance of the purple color (MnO,)) and the appearance of a brown solid (MnO;). This is similar to the Baever test for alkenes and alkynes. When the purple color (in the filter paper) is gone the reaction is complete and you can proceed. You will end up with a sodium salt solution; this is because you are in a basic pH. That is the reason why you need to add acid at the end (so you can go to the acid form of adipic acid) ESIn the cyclohexanone case you get only one product because the molecule is symmetric, but what if you had ° e ko, Now an example from an old quiz. 1) KMn0O,, NaOH, H,0, heat ‘CO>H rs 2) HCl, HO COzH (only product) A ketone ES