Question

In the late 1970's, a graduate student at a major West Coast university began synthesizing new classes of drugs and testing them on himself. After being expelled from the university, he began making his living by illegally synthesizing and selling to heroin addicts compound B, a synthetic analog of meperidine (Demerol). After shortening his synthetic procedure and self-injecting his product, he developed severe symptoms of Parkinson's disease, as did several of his young clients, one person died. Chemists found that his compound B contained two by-products, alcohol and another compound MPTP ( CHN), which, when independently injected into animals, caused the same symptoms. (Ironically, this has been one of the most significant advances in Parkinsonism research) Given the illicit chemistry outlined below, show the mechanism of formation for compound A then the mechanism to compound B N-bromo succini mide peroxides CCI, HO

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Answer 1

for benz A NBS (N-Brito succinanide) is used brotination. CHI CH3 BV JBS culul peresine act Mechanish for (W): free radical LR.br NBS lighty Br - CH2 (A)

product-B Mechanißr: (spl) - City teren Carbocation Hz (product)