Question

help please!

1) Reactions. Provide the major product for each reaction sequence, account for stereochemistry. 1) PCC, CH2Cl2 2) Brz, acetic acid OH 3) KotBu, A 4) NaOEt, EtOH P CO 8 5) H2O+ workup 6) THF, H.CaPPha HCB , cat. PdOAC) cat. PPh3, DMF, EN | CHA 0 нс. CH32) LDA, THF, -78 °C CHICH,then H3O+ workup 4) NaBH4, EtOH, then H3O+ workup 5) cat. TSOH, benzaldehyde 1) cat. H2SO4, A 2) O3. CH2Cl2, then (CH3)2S CH; 3) NaOE, ETOH 4) acetone, NaOet, EtOH, A 5) (Ph)2CuLI, THF, then H3O+ workup

Answer 1

OH GY Pec Brz CH₂ Ch ACOH x-bromination oxidation t-BuoK, AD 62 pha coef ( Naret i chim that withis reachim fl.Hgot (H₂=ppha THE michael addition followed by gruous workup cool Pn. olett lipdlo Ac) Etn LDA hick coupling heak reaction of Reduction NaBty, EOH I Thon Hzot workup i PHE -C 3. F 3.0- CH(CH3)21 Hoot wo mucleophilic addition Col-CHO I pH p4 OH 04 Some TSOH acetal formation

1. cat. Hasoy A - CH 1.03 7 El -cth 2.Dms F Etong Eton (ph) 2 Culi acetone ENTONG EtOH then Haut