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Modern Organic synthesis

Modern Organic synthesis. Mr. Anand S Burange, Institute Of Chemical Technology, Matunga , Mumbai-400019 E-mail: asgburange@gmail.com. Sir, Robert Boyle ; First man who independently started working in scientific field of chemicals now termed as Chemistry.

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Modern Organic synthesis

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  1. Modern Organic synthesis Mr. Anand S Burange, Institute Of Chemical Technology, Matunga , Mumbai-400019 E-mail: asgburange@gmail.com

  2. Sir, Robert Boyle ; First man who independently started working in scientific field of chemicals now termed as Chemistry. In 1828, when F. Wohler accidently got urea in the laboratory, from that day Organic Chemistry came into an existence NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  3. What is a chemical reaction? Chemical reaction is an effective interaction between two or more molecules/atoms /ions leading to the formation of new compound(s). NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  4. Synthesis Organic synthesis is a construction of complex organic compounds by a series of chemical reactions. There are two main areas of research in the field of organic synthesis, namely total synthesis and methodology. NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  5. Functional group interconversions Disconnection approach Asymmetric Synthesis Three main keys in organic synthesis NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  6. Functional group Interconversions (CH3 )2S+CH2-(DMSO,NaH,Me3S+ ) NaBH4/ EtOH Zn-Hg/ HCl OR N2H4 / KOH SeO2 (a) NaBH4/ EtOH (b) H+ /Heat NaOH LDA, PhSeBr/H2O2 NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  7. NaOH (Cannizaro) OR H- donor reductant • K2Cr2O7/H+ OR KMnO4/H+ • iii. CH2N2OR (a) KMnO4/H+ (b) 2eq. MeLi • (a) KMnO4/H+ (b) SOCl2 (c) EtMgBr • RhCl(Pph3)3 : Wilkinson’s catalyst • NaCN/EtOH • vii. Conc. HNO3/Conc. H2SO4 NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  8. CH2I2, Zn(Cu)/ Et2O • m-CPBA (Bartlett Mechanism) • iii. SeO2 • iv. (a) SeO2 (b) MnO2 • (a) SeO2 (b) MnO2 (c)-CH2 –SOMe2 • (a) SeO2 (b) MnO2 (c)H2O2/OH- • vii. (a) HBr (b) Mg /Dry ether (C) Ph-CHO NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  9. m-CPBA • CH2N2 • iii. (a) Cl-CH2-COOEt/Me3CONa • (b) H3O+OR Ph3P=CH-OMe • iv. (a)Mg-Hg/ TiCl4 (b) H2O • (a) H2N-OH (b) H+ • (a)Pyrrolidine/TsOH (b) CO (OEt)2 • vii. Ph3P=CH2 NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  10. Some Functional group Interconversions for practice i. 9-BBN ii. Ethanolamine i. Cl-PO(OEt)2/NaH ii. NaNH2/NH3(Via Benzyne) i. Hg(OAc)2 /H2O ii. NaBH4/ OH- i. B2H6/ solvent ii. H2O2/ OH- NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  11. Asymmetric Synthesis Alkene dihydroxylation OsO4 OR KMnO4 I2/AgOAc (dry) OR (a)m-CPBA (b) Hydrolysis Reduction Luche’s Reduction NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  12. Stereospecific cycloaddition reactions [4+2] cycloaddition reactions takes place in presence of heat NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  13. Epoxidation i. NBS ii. OH- m-CPBA NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  14. GETTING SLEEPY NOW IT’S TIME TO MOVE YOUR HEAD UP & DOWN !!ANTI PERIPLANAR RELATIONSHIP!! NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  15. DON’T GET FRUSTRATED!!! NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  16. Disconnection approach • Retrosynthesis – thinking backwards from relatively complex molecules to simpler ones – the disconnection approach originated by E.J. Corey (Nobel Prize 1990) • Terms involved • Target Molecule (TM) • The compound we wish to prepare • Retrosynthetic Analysis • The process of WORKING BACKWARDS from the TM in order to devise a suitable synthetic route. • Readily Available Starting Materials (RASM) • cheap, commercially available compounds. • Synthon • An idealised fragment, usually a cation or anion, resulting from a disconnection. • Synthetic Equivalent • The actual compounds used to function as synthons. • Functional Group Interconversion (FGI) • The process of writing one functional group for another to help synthetic planning and to help disconnection.  

  17. Chemical Equivalents (C.E.)

  18. TM (Target Molecule) NET/SET guidance lecture under UGC merged scheme at Patkar College, Goregaon, Mumbai

  19. Thank You

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