Question

3. Shown below are a series of reactions. Predict the major product for each of them. Remember, you will need to first decide whether the reaction occurs by an SN2, SN1, E2, or E1 before you can determine what the product will be. Label each as SN2, SN1, E2, or E1. Hint: First decide whether S2/E2 or S1/E1 is favored, and then decide whether the reaction pathway goes by a substitution or elimination reaction. SN2 / SN1 E2/E1 Na DMSO,rt K OtBu DMSO, rt É CI OCH Br CH3 CH3OH H20, 80 °C HEC OMS CHE Na CN CH3CN, rt HEC OMS сн. HCN H20, rt

Answer 1

1) S_N1 occurs by substitution of I^- to the tertiary carbon atom containing Cl.

2) E2 occurs by the elimination of Cl^- and production of an alkene

3) S_N1 occurs by substitution of the group OCH₃^- at the place of Br^- by the formation of a carbocation.

5) E1 elimination of OH group and formation of an alkene using H₃PO₄

10) and 11) E2 elimination of alcoholic groups (OTs and OH respectively)