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KIMIA ORGANIK FISIK

CARBON-CARBON BOND FORMATION. KIMIA ORGANIK FISIK. 2. Melalui reaksi antara C + dengan C -. Lebih terkendali, (digunakan dalam sintesis). Pembentukan Ikatan C-C. 1. Melalui reaksi radikal bebas. Tidak terkendali, dapat melakukan reaksi berantai (tidak digunakan dalam sintesis).

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KIMIA ORGANIK FISIK

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  1. CARBON-CARBON BOND FORMATION KIMIA ORGANIK FISIK

  2. 2. Melalui reaksi antara C+ dengan C- Lebih terkendali, (digunakan dalam sintesis) PembentukanIkatan C-C 1. Melaluireaksiradikalbebas Tidak terkendali, dapat melakukan reaksi berantai (tidak digunakan dalam sintesis)

  3. FREE RADICAL C-C BOND FORMATION • A. DIMERISATIONS CH3. + CH3. CH3 – CH3 POLYMERISATION ALKENES

  4. Chain branching occurs by abstraction of a hydrogen atom on the same chain and continuation of growth from the main chain

  5. SERANGAN C NUCLEOFIL (C-) PADA KARBOKATION (C+)

  6. Sumber C elektrofil • Alkil halida 2. Alkil sulfonat 3. Senyawa karbonil 4. Alkena yang berkonjugasi dengan EWG

  7. Sumber C nukleofil • Organo logam 2. Karbanion alkinil

  8. CLASSIFICATION OF C-C FORMATION 1,4- Adition (Michael) Alkenes & Alkynes Rxn Carbanion Alkylation Carbonyl Reaction C- C+ C- C+ C- C+ C+ C-

  9. PembentukanIkatan C-C a)  Carbanion Alkylation i)  Alkylation of enolate ions ii) Alkylation of acetylide or cyanide iii) Organometallic alkylation

  10. b) Carbonyl Addition And Carbonyl Substitution Reactions i)  Aldol and related reactions (Addn) ii) Claisen condensation and related reactions (Subn) iii)  Organometallic reactions (Addn)

  11. iv)  Acetylide/cyanide addition v)  Wittig reaction (Addn)

  12. c) Conjugate Addition Reactions - ‘Michael’ (1,4 Addition) d) Reaction Of Alkenes, and Alkynes i) Addition of carbenes to alkenes

  13. ii)  Pericyclic reactions: Cycloadditions Electrocyclic reactions Sigmatropic reactions

  14. REAKSI PERISIKLIK • Suatureaksi yang melibatkankeadaantransisiberupasiklik yang menyerupaikarakteraromatis • Rearrangement Cope /Sigmatropik • ReaksiElektrosiklik • Reaksi Diels Alder

  15. Yaitu migrasi dari suatu ikatan sigma pada sistem elektron phi ke suatu posisi baru. Contoh rearrangement tingkat [3,3], ikatan sigma pada karbon no 3 bermigrasi ke posisi baru yang berjarak 3 karbon Melibatkan keadaan transisi berkarakter aromatis REARRANGEMENT COPE/SIGMATROPIK

  16. Claisen Rearrangement Bila posisi ortho telah terisi, maka migrasi dapat berlanjut ke posisi para

  17. REAKSI ELEKTROSIKLIKadalahsuatusikloadisiintramolekuler, dengansuatuikatantunggalterbentukdiantaradua atom karbon terminal darisistemelektron phi terkonyugasi (atausebaliknya) • Karakteristik reaksi elektrosiklik: • Mekanismenya tidak melibatkan intermediet radikal atau ionik • Ikatan-ikatan yang dibentuk atau diputuskan dalam tahap serempak dan melibatkan keadaan transisi yang siklik • memerlukan panas atau cahaya untuk inisiasi • Reaksi bersifat stereospesifik

  18. Conrotatori :rotasi orbital p berlangsungdenganarahsama Disrotatori: rotasi orbital p berlangsungdenganarahberbeda Dalamreaksielektrosiklik, pembentukanikatan sigma barudapatberlangsungsecara:

  19. Aturan Woodward-Hoffman untuk Reaksi Perisiklik

  20. Reaksi Diels-Alder Suatu reaksi sikloadisi (stereospesifik) diena dienofil sikloheksena Diels-Alder adduct

  21. Reaksi Diels-Alder A. Mechanisme Reaksi Pericyclic :concerted reaction that proceeds through a cyclic array of electrons in the TS cyclic array of 6 p e–s

  22. The Diels-Alder Reaction Dienesand dienophiles Works best with electron-poor dienophiles (A,B,Y,Z = C=O, CN):

  23. The Diels-Alder Reaction B. Dienes and dienophiles

  24. The Diels-Alder Reaction B. Dienes and dienophiles

  25. The Diels-Alder Reaction C. Stereospecificity

  26. The Diels-Alder Reaction D. Stereoselectivity

  27. CheckAnswer The Diels-Alder Reaction Question . Draw the structure of the Diels-Alder adduct in each of the following reactions.

  28. The Diels-Alder Reaction Answer Draw the structure of the Diels-Alder adduct in each of the following reactions.

  29. CheckAnswer The Diels-Alder Reaction Question 10-6. What diene and dienophile would be used to make each of the following compounds?

  30. The Diels-Alder Reaction Answer What diene and dienophile would be used to make each of the following compounds?

  31. Tunjukkan 2 cara mensintesis aldrin

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