Question

6. Show the missing structures in this reaction sequence: PCC 1) CH,Mg! 2) H2O* CH.03 CH,203 C.H.03 PhP-CH, SCI E C.H.O.S pyridine D 1 C H 603 ) BH. THF H.O. NAOH C CH140 CH,CH_CCHCH, Spontaneous F. 130, [G] spontaneous C3H2403 COH 2003 CH,802 a-Multistriatin, an insect pheromone

Answer 1

Пснам, Рес 9. 2) ное ч, с- ск он —2HCre 3 С, Н,603 OXIDATION С, Н,403 (4 ноҳ WITTIG REACTION Phzp=cha Сн,би CH2 isci/py 1) Bна тнг — нс гCH в, 2) но, еднс - с. c8 - 10 . са и 4 C13 о 11 сч,015 см, - си с-сип, сна С. Си-сна C8 н 14 02 см3 CH, - ги -L-CP, cuz сна-сн, - нс - СН H₂O смт sor нс и, нс - ср он он С Н2401 Суд над 5 Спо Р,оо,

10/ spontaneous spontaneous T 1 C give formation of Lot or hemiacetal LOH ③ ColH2O3 [Explanation D Aldehyde reacts with CH₂ mg I followed by of Steps - hydrolysis gives - alcohol. A. 2) on PCC oxidation gives kehone ® 3) kelone on reaction with Ph3 P = CH2 [WITTIG REACTION] gives an al kene ©. 4) ® on hydroboration with BH₃. The followed by oxidation with H₂²2 / 8it gives i, alcohol ① 5) ® on reaction with Tscl/py gives tosyl derivative ② 6) Tosyl derivative © on reaction with Carbanian undergoes 1 sur reaction to give © . 7) ® on hydrolysis gives diol [ removal of acetal e) @ undergoes spontaneous reaction of carbonyl group with . -OH group to give the required hemiacetal (2-multistriation).