Question

Extra credit (10 pts) 2140 b Show how to synthesize 2-methyl-2,6-heptandiol from 5-hydroxy-2-pentanone and any other reagents you need CH он он Show how to synthesize 2-ethyl-3-methyl-1-butene using 2-methyl-3-pentan triphenylphosphine and any other reagents you need one Podut vene CH O CH CH,CH 3

Answer 1

OH Cc eNaH o H 구 OH 2-methy/-25-heptandol 342 2-ethyl-mel ろ

PCC is a mild oxidising agent and oxidize the Alcohol to aldehyde. Then Grignard reagent is more reactive towards aldehyde than Ketone. Hence grigGrig reagent gives secondary alcohol with aldehyde first then protection of alcohol by ether since OH is Grignard reagent sensitive. Then reaction of ketone with Grignard reagent gives tertiary alcohol them followed by deprotection of Ether by Lewis acid.

11. Synthesis of Phosphorus ylide with methyl bromide then Wittig reaction gives required alkene.