Allylic Oxidation and the Metabolism of Marijuana

The liver enzyme cytochrome P-450 oxidizes many toxic metabohtes and drugs at aUyhc sites. For example, an allylic oxidation is the first step in the degradation of one of the psychoactive ingredients in marijuana. Although the nature of all steps is not well understood, an allyl radical is a hkely intermediate in this process. 

T-n r nki iiir ATi-r Electrophilic addition reactions to nonconi mated alkadienes can occur at one or both double bonds. 

Inese reactions occur by 1,2-addition, and we can use Markovnikovs rule to predict the major products. 

The addition of HBr to a conjugated diene is strikingly different. Adding IM equivalent of HBr at a low temperature yields two products. 

The first step in the reaction is electrophilic addition of a proton to the conjugated diene. 

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