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 Products A and B CH3 H₂CX HAC CH3 E-l condition 4,4-dimethylhexan-3-ol

Answer 1

5 Given oganfc Molecu le OH CH3 4.4 Dimethyl herane -3-ol abore ongafc Molecole îs heated bth Concentratea phosphonfc acid to gfves Pioducts A and CH3 O4 CH7 conc Hare A снз M-condton CH3 CH3 When ever an elimMation occo a5 to gVe HOne highly sustituted the mone Stable aIkene. chemfsts say that the elimmatfon tollour a1seyls ole AcCording+o this Juke oe oe alkenes A and s mafo77 al kene M thir cactov) A

Mechantsm H3 Po4 24-canbotation unstable -CH3 Slanctep CH3 CHз Protenation еHg CH3 Rate Dagne-neeain determnéng step aearnongement CanbocatHon neanangene CH3 сHз H2 Poy CHP -CH3 3-Canbo Cahon Peproknatfon mone Stable Pnoduct A More stable al kene AlC Zaf sev'snule CH Ke cause moie stbstituted alkene .CHD Cty -CH 4с H2 POY сH HS Dep Yottnotion product B Les stoble AJkene Alc 7aiSev's ute

The elimtmation Sieaction tollows E Hechanism Vfa tormotian of a stable tentlany Conbocotfon Futermediate pehydsation of alcohol s slos Step and ate detormtntng step nthes Step only alcoha) on nvol the eacton Rate o3,3 dimetnyl Hexane 3 -ol Rate K3.3 dimetnyl Hexane 3 ol Intnis a 50 'Obsene a bi pro bluct vergweny, less amaun