Question

PLEASE HELP ME IT IS DUE TONIGHT ! write the whole reaction out neatly

ou [1] Oxidation of 1 alcohols with PCC (Section 12.12B) РСС но. 1 alcohol н R Reduction of esters (Section 17.7A) [2] о O [1] DIBAL-H OR [2] Н,о ester Reduction of acid chlorides (Section 17.7A) [3] O 1 LIAIHOC(CHab CI н [2] H2O acid chloride [4] Hydroboration-oxidation of an alkyne (Section 11.10) (1 R BH R H [2] H202, OH alkyne

Answer 1

R OH - Pec R Mechanism: R CH₂o - H err R-CH ₂ 0 0 R& R- C-H R-43046 R- CH-o-'er-o reio, H

DIBAL-H R -C- OR' H₂O Mechanism: R-e- ÖR O AL H-Al > H R- C. aquous R-C-H work R- C up

Li Al H[loc (CH3)3) Rra el R-C-H H₂O Mechanismi R 1 Liolo! 410 - R-chel Al-O R-CH → R-CH aquous work up

R-C=C-H R₂ BH H₂O2, H² Mechanism: R - C = C- H 22 - R-q=CH-BRE R-C=CH-BR2 H-B-R H HOO / H2O2, OH R R-CH=C-0-B- RL R- CH = CH - BR o-o-H I similarly H₂O OR R-CH=CH-o-Brie R-CH=CH-OH I tautomerism R- CH₂ - CHO