Br -CHO (13) НО. Br (14) -CO E (15) 1. Mel (excess) (16) 2. Ag20, H20...
with mechanism
1. xs Mel 2. Ag20, H20, heat
2) CHs LDA 1) LDA 3 2) Ci OH, H20 -OH, H2O CHO 1 LDA 2) CH3CH2Br Он, H2O 1) NaOEt 8 2) NaOEt OEt 10 Cl NaH 2 (excess) 12 HO Bra(excess) 13 HO LDA 14L THF, -78 C NaOEt, EtOH NaOEt, EtOH 16 NaOEt, EtOH 17 Br но 18 OOEt 1)NaOEt, EtOH 2) H3O 19 OEt 20 l HO o CHO + H20
Predict the major product for the following reaction.
1. excess CH1 NH2 2. Ag20, H20 heat 1. KOH 2. CH3CH2CH2CH,Br 3. H30 d. NH &
Provide the major product for the following sequence of reactions. 1. CH31 (excess) 2. Ag20, H20 3. heat
2. Predict the product. CH,CH NH2 NH 1. LiAlH 2. H20 Br H30 KOH 1. excess CH1 2. Ag20, H20 heat
2. Predict the product. CH,CH2NH2 1. LIAIH NH 2. H20 Н,о" Br КОН NH 1. excess CH3I 2. Ag20, H20 heat
transformation
OAc OAc AcO Aco Aco OCH2CH2Ph OAc OAc e) CHO OH 1. HCN 2. H17/H20 3. Na/Hg но CH2OH
OAc OAc AcO Aco Aco OCH2CH2Ph OAc OAc e) CHO OH 1. HCN 2. H17/H20 3. Na/Hg но CH2OH
Draw the major product of the following Hofmann elimination. CH3 H3C-1 1. Ag20, H20 excess 2. heat CH3
OH r. Он reagent(s) Br OEt S. reagent(s) Br Он K2Cr2O7 (excess) H2SO4, H20 Он но 1. PhLi, Et O 2. HCI, H2O 3. SOCI2, EtN 4. NaOAc u. н 1. Mg (1 eq), Et2O V. Br 2. (1 eq) -сно 3. HCI, Н,О W. 1. NaBH,, MeOН, 0° С 2. PBra THF 3. LIAID4, THF 4. HCI, H20
Predict the products.
16. K2Cr207 (excess) H2SO4, H2O HO 1. Phli, Et20 2. HCI, H20 3. SOCI2, Etz 4. NaOAC 1. Mg (1 eq), Et O Br 2. (1 eq) | C-CHO 3. HCI, H20 1. NaBH, MeOH, 0°C 2. PBrz. THE 3. LiAIDA, THE 4. HCI, H20 1. SOCI, NEtz, THE CHO 2. 2 eq Li, hexane 3. HCI, H20 hint: multiple steps 1. LiAlH4, THE 2. HCI, H2O 3. PBr3, THE 1. PCC, DCM OH 2. Mg, Eto...