O◇CHOCH,CH=CH,←CHON,BCH,cH=CH, CHONa&CHOH。◇CH,Br←+BrCH,CH=CH CH3 (10)CHaCOCH3 HC=CH_KOH HC=C-OH CH3CH3 CIKON HOCC OH LM C HOCCOH CH3 CH3 CHs CH Hs0头产物 (）O-CcCH,cH年KoRo"CH-CHaH/OR CCCCLLC-CCCC cmdon aa82-c8,肥X CH3 CHO 0X0i←aHa0·3cHcH0 0C2H5 QC2Hs 0 8HGH,GH,CHeBr·HCCH.CHCH←HOCHS,CH.CH.CH CHs CHz=CHCH2CHs 0C2H5 MgBr」 0C2H5 0C2H5 COCH310 CH2OCH2 CH2 + ONa (9) CH=CH2 BrCH2CH=CH2 CH2ONa CH2OH + BrCH2CH=CH2 CH2Br (10 ) CH3COCH3 + HC CH KOH HC C C CH3 CH3 OH CH3COCH3 KOH C C C CH3 CH3 HO C OH CH3 CH3 Lindlar.Cat. C C CH3 CH3 HO C OH CH3 CH3 C H2SO4
✾ 11 ✿ CH2=CH2 CH2CH3 Cl2 /❀ KOH/ROH CH=CH2 CH2CH2Br HBr/ROOR HC CNa CH2CH2C CH CH2CH2CCH3 O H2O/HgSO4 /H+ HNO3 /H2SO4 CH2CH2CCH3 O NO2 Cl2 /Fe ❁✦❂ CH3 O O CH CH3 CH O O OH OH + (12) CH3 CHO HO HO CHO CH3 + CH3 CHO 2 CH3CHO OH OH HO HO CH3CHO + 3 CH3CHO C2H5 OH O (13 ) CHCH2CH2CH3 OC2H5 C2H5 MgBr OC2H5 + HCCH2CH2CH3 CH2=CHCH2CH3 HOCH2CH2CH2CH3 C2H5 OH C2H5 MgBr OC2H5 Br OC2H5 COCH3 OC2H5 OC2H5 Br COCH3 OC2H5