-NH2 PCC, CH2Cl2 NaBH CN OH 8 Br 1. 3 equiv. 12 4 equiv. NaOH 1. LiAlH4 2. H2O 2. H30* 9 10 2 equiv. (CH3)2NH 1. LiAIH 2. H20 11 12 H2O 1. CH,MgCI 2. H30 13 14
Br 1. 3 equiv. 12 4 equiv. NaOH 1. LiAlH4 2. H2O 2. H30+ 10
O Ç(CH3)3 1) CH3CCI, AICI: 2) (CH3)2NH H2, Raney-Ni, heat CO Me 1) PhMgBr (2 equiv.) 2) H2O, H30+
draw the major product 11. Ç(CH3) 30 1) CH3CCI, AICI 2) (CH3)2NH H2, Raney-Ni, heat 12. ÇO Me 1) PhMgBr (2 equiv.) 2) H20, H,00 13. CNH2 1) Brz, NaOH, H20 O 11 2) CH3CCI, pyridine
Predict the product for the following reaction sequence. 1. O (CH3)2NH 1. LiAlH4 2. H3?
give major product O 11. Ç(CH3)3 1) CH3CCI, AICI: 2) (CH3)2NH H2, Raney-Ni, heat 12. ÇO Me 1) PhMgBr (2 equiv.) 2) H20, H30 13. CNH2 1) Brz, NaOH, H20 2) CH,CCI, pyridine 14. HNO3 CHO но +н н+он н+он нон CH OH оо 15. H2NCO, 1) (CH3),COCOCOC(CH3)3 Ph -N: C: NH- PhNHNH | 16. CHO HOTH HOH (3 equiv.) H-OH HO+H CH2OH ai
CH3 Heat KMnO4 NaOH SOCI2 3) 16) H2O (CH3)2NH CH:C00 8) CH3OH AICI (CH3)2Culi NaOH 11) LAH (CH:CO), 14) 13) CH3COCI
1. CH MgBr 2. HO 1. (CH3),Cuti 2. H2O 1. CHg MgBr 2. H20 1. (CH3)2NH 2. H20 2. H20 1. CH CHANH, OCH,CHE 2 HO CH OH • Sul
find major product for each O Ç(CH3)3 1) CH3CCI, AICI = 2) (CH3)2NH H2, Raney-Ni, heat CO2Me 1) PhMgBr (2 equiv.) 2) H20, H30*
1. (CH3)2NH 2. LIAIH4 3. H2O N O of NK CN NH2 O