Question

5. Predict the eliminations products A and B formed (El mechanism) when 4,4-dimethylhexan 3-ol is heated with concentrated phosphoric acid. Also, identify the rate determining step and the major product using Zaitsev's Rule? (Mechanism must be shown to receive full points) (20 pts) ОН conc. H3PO4 CH3 Products A and B H₂CX HAC CH3 E-l condition 4,4-dimethylhexan-3-ol

Answer 1

OH CH3 OH Н3САУСНЫ H. CH CH3 - H3C CH3 H3C CH3 H30 H3C CH3 H H3CYCH H3C CH3 Minor product Rearrangement of carbocation CH, shift CH3 H2CYCH CH3 CH3 HCACH3 CH3 Major product CH3 Stable tertiary carbocation Rate determining step Zaitsev's rule predicts that in an elimination reaction, the most substituted product will be most favored.