Question

21) Dehydration of 1-butanol with concentrated sulfuric acid at 140°C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid? A) The reaction undergoes an E2-type elimination mechanism. B) The reaction follows a new mechanism involving the formation of a carbanion intermediate. C) The reaction undergoes an El-type elimination mechanism in conjunction with a hydride shift. D) The reaction undergoes an E2-type elimination mechanism in conjunction with a methyl shift. E) The reaction undergoes an E1-type elimination mechanism with no shifting. Bonus question (10 points) 22) Propose a mechanism with a hydride shift for the solvolysis reaction below (include all necessary arrows). Br но CH3 CHa heat faconc shown осняа coc HCOCHC KHcoCHaC ermined from owing carbocation -O

Answer 1

HO 140°C Reaction Mechanisme W e hope that rapat HINH Hydrible im Shift towards 2o to io 8–8–0+ towards 20 to 10 SOI z-butene more stable product li so Answer © is correct Answer

22 Reaction Mechanism? due to the allylic - Carbocation more stable ou Brg --CHE -CHS Hydride in I migrating takes Place