Question

Q 2. Show how each of the following compounds can be prepared from the given starting materials using retrosynthetic analysis approach. a) Available starting materials (source of carbon) H CH3NO2 Available starting materials (source of carbon)

Answer 1

Step- OME ime -H 4 NO2 vey H H h Home MO2 앤 си, This step is hengey reaction. First â beese abs tococos acidic proton from a carbon atom oY - NOL. The carsanion is formed which reacts with aldehycle and forms a hydroxy Ninio pentane. Step II =) on on. NO2 676 cha H on. you ou. — Си CH ой ou HD SH no H₂O

on. on. oziv on CAN Den - CH 40 inson Con - NowH. sn cos 10 и OTS. Step I is ney reaction • Beise abstracts a-Carbon proton and forms tine charged Carbanian, ion which resonates with Mitrogen OJNO2. Then by proton abstraction imonium ion is formed which is attacked by crater molecule to form aldehyde. There is an hydroxide group is present which can be further reacted with Toseph which converts -on into -OTS This -OTS is good leaving group and on nucleophilic attack it leaves fastly. chorice

Step It LDA 9 to- LDA - Lithium di iso propyl amine. cus Cho uç Cuz OTS. eTs product. Step II involue &-H abstraction from a hindered base. This abstract proton from last substituted side to avoid hinderence between carbon chaine. This forms a enolate. This enolate from Carbon side attacks at - Ots maki -OTS leave and pet preocluct making is formed.