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Chapter 24: Synthesis Name: 1. Complete the reaction scheme. H₂C. 1. HONO 2. Cuci 1. Mg....
complete the following reactions with the proper stereochemistry as need оCHbb H2SO4 (dilute) OH H2O HBr (conc) но H но heat но но H CHs MCPBA OH Jones (CrO3. H,SO4) H2O, acetone 1. MCPBA OH PCC 2. NaCN 3. Hy0 pyridinium chlorochromate CH2CI2, 25 C 1. MCPBA PCC OH pyridinium chlorochromate 2. HBr Cн-Cl, 25 C NaBH OH Hао 1. DMSO, (COCI)2, -60C 1. LIAIH 2. Et N 2. H,0 оCHbb H2SO4 (dilute) OH H2O HBr (conc) но H но...
4. Predict the products for the following reaction sequences. OH H SOCI pyridine (CH3)2NH 1. LIAIHA 2. H20 CH,CH,Br NH2 base (-HBr) CH3Br base (-HBr) o cum, quod cas merea, moms outlet V i har hatteNaensen mCPBA (a) LIAIH4 (b) H20 NaBH,CN NH2 H2SO4
3) Complete the following synthesis 1 eq. DIBAL CN K) 78 C H2o 3) Complete the following synthesis A) H+ он OH NaNH2 OTs OTs PCC PCl 1 eq. DIBAL CN K) 78 C H2o 3) Complete the following synthesis A) H+ он OH NaNH2 OTs OTs PCC PCl
2. Complete the following reaction scheme. 1.0 2. Mes POCIE pyridine NaBHA ELOH (CH3)2Culi SOCIO H,O*, heat Br NaCN 1. LIATHA 1. DIBALH 2. H30* acetone 2. H2O CHAPTER QUESTIONS - CHAPTER 19 1. DIBALH 2. H30* HCN non nour under acidic or basic conditions. Write two example
Chapter 19: More Reactions Name 1. Complete the following reaction scheme. 1.2 eq. MeMgBr 2. H2O* TMSCI pyridine n-Bu NF POCI pyridine HyC-PP 2. Synthesize the following compound starting from cyclohexene. 3. Complete the following reaction scheme. Determine if the reaction proceeded through direct or conjugate addition CH,NH2 1. LiBu 1. EtMgBr 2. H30 2. H30* 1. (CH3)2Culi 2. H30* 29
1. SOCI, NEt3, THE 2. 2 eq Li, hexane 3. HCI, H2O CHO Br hint: multiple steps B TH 1. LIAIH, THE 2. HCI, H2O 3. PBr3, THE CN OH 1. PCC, DCM 2. Mg, Et O 3. HCI, H2O 1. MSCI, pyr 2. KO'Bu, 'BuOH
K2Cr207 (excess) H2SO4, H2O HO OH u. 1. PhLi, Et20 2. HCI, H2O 3. SOCl2, Etz 4. NaOAC 1. Mg (1 eq), Et20 Br 2. i (1 eq) -CHO 3. HCI, H20 1. NaBH4, MeOH, 0°C 2. PBr3, THE 3. LiAID4, THE 4. HCI, H2O x. 1. SOCI, NEtz, THE CHO 2. 2 eq Li, hexane 3. HCI, H2O hint: multiple steps 1. LiAIHA, THE 2. HCI, H20 3. PBrz, THE a1. 1. PCC, DCM OH 2. Mg, Et20 3....
K2Cr2O, (excess) HASOHO 1. Phli, Et 2. HCI, H2O 3. SOCI, EIN 4. NaOAC 1. Mg (1 eg). Et, 2. i (19) -CHO 3. HCI, H20 1. NaBH4, MeOH, 0°C 2. PB.. THE 3. LIAID, THE 4. HCI, H20 1. SOCI, NE. THE 2. 2 eq Li, hexane 3. HCI, H20 Pintuicio sops 1. LiAlH. THE 2. HCI, H2O 3. PB. THE 1. PCC, DCM OH 2. Mg, Et20 3.HCI, H20 1. MsCl, pyr 2. KO'Bu, 'BuOH
B12 1.D SOCI Mg THE G- Light 3. A recent reporting forming cart than OH 2. H2O 1. LAH, THE H Cro MeOH - М 2. H2O excess 2. Fill in structures for A-O in the following reaction scheme part of which was recently reported in the chemical literature (JOC, 2011, 57-64). (15 x 3 = 45 pt) CH3OH KMnO4 1. LAH A B НО heat 2. H2O Cro, ci
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...