7) A nucleophile can attack acrolein either at the terminal carbon or at the carbonyl. Draw...
7) A nucleophile can attack acrolein either at the terminal carbon or at the carbonyl. Draw a) the mechanism for each addition as labeled, b) the inital intermediate formed, and c) the final product formed after neutralizing aqueous, mild acidic, workup. 1,2-addition a Nob) is also called 1,4-additiona) is also called d) Explicitly state why coulombic or FMO factors determine the course of each reaction. 1,4-addition: 1,2-addition: e) A hydride like NaBH4 would do a 1,4-addition or 1,2-addition? f) A thiolate would do a 1.4-addition or 1,2-addition? g) What theory explains the regioselectivity above (full name)? h) Build the acrolein FMO diagram from C= C i) Then draw and label the HOMO or LUMO of and C=O (similar to butadiene from 2 ethylenes) acrolein that dominates FMO reactivity. Find the values for localized charge density on acrolein and compare to relevant FMO coefficients. C2-01 Ca=c C4-C3-C2-01