Question

5. Predict the eliminations products A and B formed (E-1 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. H2PO4 Products A and B CH3 H₃C X E-1 condition H3C CH3 4,4-dimethylhexan-3-ol

Answer 1

tz Controly CH3 Cty El eliniute as CH CH3 PH strow) mixture CH3 Contapoy, Ho - He Cha CH3 Celta I e elimination, loss of the leading group to carbocation A rate determining step Slow step -20 Rate determing Step CHS 2 carbo Cutron 11,2-methul group T shift Goltz) CH2 you - Citz I carbocation. more stable en Elly + 4300 - Ck you the 6 Tetra substituted Alkenes are more stable them di-substitued. According to zaitser rule, the more substituted alken is the major product. This is because of the transition state leading to the more substituted alkene is lower ly energy and therefore will proceed at higher rate