Question

Predict the Major product(s) for the following reactions and draw their corresponding arrow-pushing mechanisms. If there is no reaction write NR. (21 points total) detailed Show the correct stereochemistry when needed KOH THF substitution Cl Mechanism: MeOH substitution Mechanism: CI t-BuOK, DMF heat elimination Mechanism:

Answer 1

If it follows SN2 substitution which follows inversion of stereochemistry (R- to S- isomer) resulting in the following product он HO K S KC If it followS SN1 substitution which produces racemic product due to the formation of carbocation Back side attack QH HO K Front side attack This is SN2 substitution which follows inversion of stereochemistry resulting in the following product. Here, the inversion happens only at the reacting site not otherwise MeOH HBr t-BuOK is a bulky base hence it plucks proton from less hindered carbon to undergo elimination + KCIt-BuOH DMF, heat BuO K NR DMF, heat