Having strange reactions to Adderall?

Adderall and its reactions. O-Chem?

• Hey guys, i'm in organic chem and i'm attempting to finish my project. However, these reactions are killing me. I'm pretty sure i can do these i'm sure running out of time and need/want some sleep before my finals tomorrow. so the drug i'm doing is Adderall. It's a common drug among in college and many kids have become reliant on the drug. "that's partly why it caught my interest" i have to find out what part of the drug will react with: 1) NaOH 2) Oxidation 3) HCl 4) Br2 5) Reduction with Hydrogen (H2/Pt) 6) Reaction with HBr ( Markonikov’s Rule) Thanks a million. -James

• Answer:

  Given that this is the correct structure of the drug: http://www.pharmacy-and-drugs.com/molecular/adderall.gif I don't know if I know ALL of them, but this is my shot: 1. No reaction comes to mind. 2. Amines can be oxidized. Depending on what reagents you use, you could end up at different products in different stages. See the following for more information. http://www.transtutors.com/chemistry-homework-help/nitrogen-containing-compounds/oxidation-of-amines.aspx 3. You'd need to check on pKa values, but I think the NH2 group would be protenated by the H+ in HCl, leaving you with NH3+ instead of just NH2. 4. Electrophilic aromatic stubstitution will occur. You'd need to add FeBr3. Alkyl groups (the branch off the aromatic ring) are inductively donating, and activating; it would direct any electrophilic substitution towards the ortho or para position (either position directly adjacent to the branch or the one completely opposite to it). It would add a Br to the aromatic ring in one of those places. (Note that Br is a deactivating group, so you'd probably only add Br once - likely to the para, or opposite position, as it has less sterics). 5. The only place to reduce is in the Benzene ring. Reduction by Hydrogen in the presence of a basic metal catalyst will not work on an aromatic ring, because aromatic rings are very stable and unreactive compounds. So basically, your drug will not react under H2/Pt conditions. If you had, maybe Rhodium catalyst instead, of some extremely high pressure/temperature/time conditions, you could possibly reduce the aromatic ring (basically remove the double bonds). 6. Very likely no reaction. If anything occurs, see #4 - Again, you'd need some additional catalyst/activating reagent.