1559r.ah23_409-42210/19/0520:17Page416 EQA 416.chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATON CH O CH.CO.CH.CH) CH:C (c)A sequence identical to that of(b),but substitute two alkylations with BrCH,COCH,for the two Michael additions to CH2=CHCOCH3. 00H 35.(a)(CH3)CH-C-CH-CH(CH3) (b)CoHs-C-CH-CoHs c-ce CoHs H CoHs In the same order as in Problem 35: O OH (a)C.H-C-CH-CH(CH (b)CoHsCCH-CaHs (ame product!) ac-c-m○ dCHC-CH-CH,CH 37.(a)A IR:Ketone and alcohol groups(cannot be an amine because molecular weight is an even OH O NMR:CH-CH CH-C- 1.4d42g220(c) A sequence identical to that of (b), but substitute two alkylations with BrCH2COCH3 for the two Michael additions to CH2PCHCOCH3. O OH B A 35. (a) (CH3)2CHOCOCHOCH(CH3)2 O OH B A (b) C6H5OCOCHOC6H5 (c) O OH B A (d) C6H5CH2OCOCHOCH2C6H5 36. (a) (b) In the same order as in Problem 35: O OH B A (a) C6H5OCOCHOCH(CH3)2 O OH B A (b) C6H5OCOCHOC6H5 (same product!) (c) O OH B A (d) C6H5OCOCHOCH2C6H5 37. (a) A IR: Ketone and alcohol groups (cannot be an amine because molecular weight is an even number). Structure is CH3CH CH3 (C4H8O2) C OH O CH3 1.4(d) 4.2(q) 2.2(s) 3.7 NMR: CH3 C OH O CH C6H5 C CH O OH S S Li
C6H5 S H S C6H5 C O OH CH 1. NaOCH2CH3 Michael 2. CH2 CHCOCH3 CH2(CO2CH2CH3)2 CH3CH2O2C CH CH2 CH2 CH3 C O CO2CH2CH3 416 • Chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATION 1559T_ch23_409-422 10/19/05 20:17 Page 416