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Problem set 2 Show the retrosynthetic analysis and forward synthesis of the following compounds. H2N

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1. Retrosynthesis C-N bond forming H2N 1 HOR HO + H reduction - –NH FG HO- FGI FGI OH reduction Reimer-Tiemann - HO HO- HOM F

2. Retrosynthesis OH C-N bond fomation C-N bond fomation a Ci Ci Etherification c1 cl FGI Synthesis Он с NaOH NH2R CW C1 C1 Z

4. Retrosynthesis NH + NH2 → CMNH2 Synthesis a to 1. H+ 2. NaBH3CN 2. NaHSCN. ethyl iodide ci

5. Retrosynthesis NH2 OH Reductive -amination OH OH Oxidation C-N bond forming OH reduction HN HO- HO HO- + HO- -NH, FGI -NH,

6. Retrosynthesis FC acylation thioetherification SH co-chau-ao o tomam- Synthesis 1. Thiourea 2. Na2co3 Br AICI3 Br2, ACOH S

7. Retrosynthesis MgBr НО O OH/ Syntheis MgBr HOLI Ether PCC, DCM PCC, DCM Mop O Na+ 8. Retrosynthesis MgBr rin $AN ang buon

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Problem set 2 Show the retrosynthetic analysis and forward synthesis of the following compounds. H2N
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