Question

Use the reagents below in the proper order to convert 3-methyl-1-butene to 2-methyl-2-butene. You may assume that all steps produce exclusively the major product. The synthesis can be accomplished in fewer than 4 steps. e.g. if you think this can be accomplished using sodium ethoxide and then potassium tert-butoxide, you would write your answer as 49. HBr 1) Hg(OAC)2, H2O H2SO4 NaOCH2CH3 H20 2) NaBH4 2. H30+ HBr 1) BH3 Br2 KOC(CH3)3 H₂ H2O2 2) H2O2/OH- Pd/C

Please explain how you got your answer in detail, and why the other answer choices are incorrect. Thank you !

Answer 1

13 1) Hg (OAC)2, H20 2) NaBH4 3)_42.50 ch CH3 3 methyl-1-Butene 2-methyl-2 Butene Mechanism CH3 LOAC CH3 Hg COAC so HAC V B Hao HOOAC) Hz o OAC OAC CH NaBth HS 1. ita cong . He 07 OH Metal Reduction : . 111. .FH3 - CH3 JA OH

CH CH3 H2504 و WHO تعلیم CN2 OH Dehydration reaction H2564 -+ 40 +H50m 왜? X CH3 HO SCHE OH H₂E A dehydration 1.1 hydride 13 1.9 hydride chą H Tentazy Carbocahon more stable Secondary carbocatim less steble ÇH3 H SO - CH3 I tha CH3 als A enation 2 Methyl 2-Butene Major product CH3 Minor alsoformed product