Question

(45 pts) What is the expected major product of the following.reaction sequence? 1 NacEL HOEt heat 2 HgrCAc) CH,OH 3 NaliH NaCH OCH3 OHH HyCO OCH3 IV- II II . (4.5 pts)Which is the correct sequence of reaction steps necessary to complete the following transformation? Br OH + enantiomer OH I. MCPBA II. NaOCH,CH. CH,CH,OH T. H,O" or -OH IV. 1) OsO, then 2) NaHSOH,O I then IV B) I then II then III C) II then I then III D) III then I E) I then IV then II then III

Answer 1

NODEEMDEE ELO pat * OEL elimination substituted pat (Maja product) (minor product) with a strong barer soduin ethorede, NaoEt elimination. predominates over substitution dimination can occan from both ß hydrogen, but the hydrogen eliminates which leads to more substituted alkene. Hg OAC) genes CHLOH y con böht Aco-tig-OAC DAC Oh Nabny napH chide (H) transfen) A60 Ha ост, I " I is the correct options, but Question adoption are a bith different, I think, there should not be only I methyl c-2 group at McPва u Nao CoHS, (a 450 Si (2450H 8GHS

oth На 0 1o-H Ent 케에 o-H trans did (c) Therefore correct II then, I option is then III
In first question, the attack of CH3OH in presence of Hg(OAc)2 is an oxymercuration demercuration reaction which follows markovnikov reaction hence attack of CH3OH takes place at the carbon which has less number of hydrogen atoms.