Question

2. Compound X, with chemical formula C Ho, gives 1,3-dimethylcyclopentane when treated with Hz Over Pt. That same compound, when treated with hot and concentrated KMnO, produces carbon dioxide and Y. Compound X reacts with two equivalents of HBr in the presence of a peroxyether to form compound Z, with chemical formula C H2Br2. When pound Z is heated in methanol it yields compound W, among others. (a) (6 pts., 3 pts. cach) Provide the structure of compounds X and Z? (b) (5 points) Show a detail mechanism for the conversion of compound Z into W. 1,3-dimethylcyclopentane H/P+/ | KMnO, (C7H10) (conc., warm, acidic) HBr / ROOR (2 equivalents) CH,OH heat OCH, (CH2317) compound X : Y compound 2: communal x. Br anae mechanism (could have ena nkowo) Lahat
please show a detailed mechanism from X-Y, X-Z, Z-W.

Answer 1

# 7 to w MH ca st Y st Bomnist CH₂O4 By I Cestar Solvent ) (Solvolysie) gine 7 carbocention Unstable 2-carbocation Etable than fo carboration but less stable than -carbocation Solvated Bromide la [1,27 n shaft BE Cozon Schand - Br solvated 30 carbocation on the Bi kucheophile 7an for Hyperconjugation (less Nuchophilic) Bo 47 ome - Otom ome