Question

1- bromo-2-methylkydopentane can be converted, through a multistep synthesis, to a compound with exactly four resonances in its (proton-decoupled) 13^C NHR spectrum. Suggest a synthetic pathway to prepare such a compound from 1-bromo-2-methylcyclopentane. 1) t-BuOK: 2) HBr, ROOR: 3) CH_3CH_2CCNa 1) EtOk: 2)H_2/Pt 1) NaCCH: 2) 9-BBN: 3) H_2O_2, NaOH 1) NaOEt: 2) HBr: 3) t-BuOK 1) NaOEt: 2) NBS, hv: 3) NaSMe 1) NaOEt: 2) BH_3 middot THF: 3) H_2O_2, NaOH Draw the product of the reaction.

Answer 1