1559T_ch19_344-35710/17/0513:51Pa9e351 ⊕ EQA Solutions to Problems351 OH -H Intermediate :0-H 0: R-6RR-C6 Altematively.intermediate 2 could protonate on the unlabeled OH group instead of the OR' group: H OH 0: R- C-R'RC-ORR-C-OR() 62H ⊕ Ester containingin the carbonyl oxygen.Now if you follow the hydrolysis mechanism written above,the product will be 1*0 R-C-1%OH! 0 0 99 32.(a)CH.CHaCCl:(b)CHaCHaCBr:(e)CHCH.COCCH2CH 0 (d)CH,CH2COCH(CH3):(e)CH3CH.CO- (CH.CH,CNHCH (g)CH,CH2CH2OH Br (h)CH;CHCO2H 33.()-coct: Solutions to Problems • 351 (b) Alternatively, intermediate 2 could protonate on the unlabeled OH group instead of the OR group: Ester containing 18O in the carbonyl oxygen. Now if you follow the hydrolysis mechanism written above, the product will be 18O B ROCO18OH! O O OO B B BB 32. (a) CH3CH2CCl; (b) CH3CH2CBr; (c) CH3CH2COCCH2CH3; O B (d) CH3CH2COCH(CH3)2 ; (e) (f) (g) CH3CH2CH2OH; Br A (h) CH3CHCO2H 33. (a) (b) COCl; COBr; CH3CH2CNHCH2 ; O CH3CH2CO H3NCH2 ; O 18 OH2 R OR R C 18 O H OH2 R OR C HO C OR (!) H, H2O 18 O H, H2O R 18 R OR C OH C O H H O H 18 O R OR OH OH C H2 18O R OR C O H R OR C H H 18 O H H Intermediate 2 1559T_ch19_344-357 10/17/05 13:51 Page 351