1559r.ch17.304-32211/3/0s10:48Page317 EQA Solutions to Problems317 (g)and (h)No reaction.These are reactions of aldehydes only. HO CN CH.H -CH2CH3 +-O ⊕ 47.The reaction occurs under acidi onditions.Therefore 19.In excl is the preferred one 00…(g) and (h) No reaction. These are reactions of aldehydes only. (i) 46. 47. The reaction occurs under acidic conditions. Therefore: 48. 49. In each case insert O on either side of the carbonyl C. Then refer to the information on migratory aptitutes in Section 17-13 to help you choose the preferred product. In the answers below, the first structure is the preferred one (a) (b) CH3 O O CH3 O OCCH3 O H O COCH3 H O O O HOCR OCR O HO
O O O O O O R H C See solution to Problem 47 O R H


R O H R R O R R H O O O O R H H O O R R O O R H O O R CH3 C
H2O N N H H HO HO OH

HOH H OH CH3 C N N CH3
H2O C N H N H
CH2CH3

HOH Irreversible loss of N2 C CH3 N H N C CH3 H CH3 C N NH H OH HO CN Solutions to Problems • 317 1559T_ch17_304-322 11/3/05 10:48 Page 317