Chem 345 PSet 08 key

Chem 345 PSet 08 Key 1.) Draw the mechanisms for the following transformations: A 1.) PhMgBr, Et2O 2.) H3O + O Ph OH O B O OH Ph 1.) excess PhLi Et2O 2.) H3O + O Ph + OH C N 1.) PhMgBr, Et2O 2.) H3O + O Ph D O 1.) LiAlH 4, Et2O 2.) H3O + OH E O O 1.) LiAlH 4, Et2O 2.) H3O + OH + OH F O OH 1.) LiAlH 4, Et2O 2.) H3O + OH G O N H 1.) LiAlH 4, Et2O 2.) H3O + N H 2.) Write the mechanisms for the following reactions: A O O O O O H O B Δ NH2OH, HCl H2SO 4, H2O O O N H 3.) What is the shape of the signal of the indicated proton (singlet, doublet etc…)? triplet pentet A B C sextet singlet D quartet E doublet of doublets of quartets Br F Br CH2's are homotopic, so they not visibly split one another CH's are enantiotopic, so they not visibly split one another J=14,10,7,7,7 4.) Fill in the boxes If multiple steps are needed, be sure to use 1.) and 2.) to differentiate different steps Be sure to watch where the arrow points O 1.) Δ, NH2OH, HCl, H2SO 4, H2O 2.) LiAlH 4, Et2O 3.) H3O + NH Beckmann followed by LAH reduction O 1.) RCO3H (or other peracid like mcpba) 2.) LiAlH 4, Et2O 3.) H3O + HO Baeyer-Villiger followed by LAH reduction OH