1559T_ch23_409-42210/19/0519:50Pa9e419 EQA Soufionso Problems419 CH -C-CO2CH2CH3 ,29a,c4, CH CH2CH2CH2CHs 〉-co,cH,c CH.CH-CH-CH CHa(CH2).CO.CH-CH CO.CH-CH c) CH.CH-CH CH-CH=CHz 上8ca CO2CH2CH; —C0,CH,CH -CH2CO2CH2CH3 0 d 0 -CH.CO-CH-CH CO2CH2CHs CO2CH2CHs CH:CHQ 22《 >CH2B 0 CO2CH2CH3 CO2CH2CH3 CH3CH20 42.Ethanol is the reaction solvent unless specified otherwise. Cyclopentanon HCO.CH.CH,+CH.CO-CH.CH,HCCH.CO.CH.CH. CH,CCH,BrCH.CCH, Solutions to Problems • 419 (b) (c) (d) 42. Ethanol is the reaction solvent unless specified otherwise. Cyclopentanone Br2, CH3CO2H BrCH2CCH3 O CH3CCH3 O Claisen HCO2CH2CH3 CH3CO2CH2CH3 HCCH2CO2CH2CH3 O Double Claisen 1. 2 NaOCH2CH3 2. 2 CH2Br CO2CH2CH3 O O CO2CH2CH3 CO2CH2CH3 CH3CH2O O O CO2CH2CH3 CH3CH2O 1. NaOH, H2O 2. H, H2O,  CH2 CH2 O O CH2 CO2CH2CH3 CH2 CO2CH2CH3 O O 2. BrCH2CH CH2 1. NaOCH2CH3 CO2CH2CH3 Dieckmann O CO2CH2CH3 CO2CH2CH3 1. NaOH, H2O 2. H, H2O,  CO2CH2CH3 CH2CH CH2 O CH2CH CH2 O Mixed Claisen CHCO2CH2CH3 CH2CH2CH2CH3 C O CO2CH2CH3 CH3(CH2)4CO2CH2CH3 1. NaOCH2CH3 2. CH3I CH3 CO2CH2CH3 CH2CH2CH2CH3 C C O 1. NaOH, H2O 2. H, H2O,  CH3 C CHCH2CH2CH2CH3 O 1559T_ch23_409-422 10/19/05 19:50 Page 419