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Asam karboksilat

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Asam karboksilat

  1. 1. ASAM KARBOSILAT DAN TURUNANNYAKerangka Dasar Asam Karboksilat dan Turunannya•HALIDA ASAM•ESTER•ANHIDRIDA ASAM•AMIDA•NITRIL•ASAM KARBOKSILAT
  2. 2. ASAM KARBOSILAT DAN TURUNANNYATata nama Asam Karboksilatada 4 macam type:1. IUPAC2. Trivial3. Asam karboksilat4. Konyugasi5. Garam KarboksilatSistem Penomoran:IUPAC: TRIVIAL:
  3. 3. ASAM KARBOSILAT DAN TURUNANNYATata nama Asam Mono Karboksilat:Struktur IUPAC TRIVIALAsam metanoat Asam formiatAsam etanoat Asam asetatAsam propanoat Asam propionatAsam butanoat Asam butiratAsam pentanoat Asam valeratAsam heksanoat Asam kaproatAsam heptanoat Asam enantatAsam oktanoat Asam kaprilatAsam nonanoat Asam pelargonatAsam dekanoat Asam kaprat
  4. 4. ASAM KARBOSILAT DAN TURUNANNYATata nama Asam Mono Karboksilat:
  5. 5. ASAM KARBOSILAT DAN TURUNANNYANama Karboksilat:Nama Konyugasi:Garam Karboksilat:
  6. 6. Tata nama Dwi Asam Karboksilat:Struktur IUPAC TRIVIALAsam 1,2- etanadioat Asam oksalatAsam 1,3-propanadioat Asam malonatAsam 1,4-butanadioat Asam suksinatAsam 1,5-pentanadioat Asam glutaratAsam 1,6- heksanadioat Asam adipatAsam 1,7-heptanadioat Asam pimelatAsam 1,8-oktanadioat Asam suberatAsam 1,9-nonanadioat Asam azelatAsam 1,10-dekananoat Asam sebakat
  7. 7. ASAM KARBOSILAT DAN TURUNANNYATata nama Halida AsamTata nama Anhidrida Asam
  8. 8. ASAM KARBOSILAT DAN TURUNANNYATata nama EsterTata nama Ester Siklik (Lakton)
  9. 9. ASAM KARBOSILAT DAN TURUNANNYAAmida PrimerAmida SekunderAmida TersierNitril
  10. 10. ASAM KARBOSILAT
  11. 11. ASAM KARBOSILATKeasaman asam karboksilatKeasaman asam karboksilat dipengaruhi oleh adanya faktorInduksi
  12. 12. Keasaman Derivat Asam BenzoatPosisi orto: efek sterik dan elektronik; Gugus pendorongelektron (m dan p) < keasamanSTRUKTUR POSISI SUBSTITUEN DAN pKAORTO META PARA4,2 4,2 4,23,9 4,3 4,43,0 4,1 4,54,1 4,1 4,52,9 3,8 4,02,9 3,8 4,02,2 3,5 3,4
  13. 13. TRANFORMASI ASAM KARBOSILAT
  14. 14. REDUKSI ASAM KARBOSILATMekanisme Reaksi
  15. 15. REAKSI ESTERIFIKASIMekanisme Reaksi (Reaksi substitusi/Adisi-Eliminasi)
  16. 16. PEMBENTUKAN HALIDA ASAMMekanisme Reaksi (Reaksi substitusi/Adisi-Eliminasi)Transformasi asam karboksilat menjadi halida asam selain SOCl2 dapatmenggunakan HCl, PCl3 atau PCl5
  17. 17. PEMBENTUKAN ANHIDRIDA ASAM
  18. 18. DEKARBOKSILASI ASAM β-KETO DAN DWI ASAM
  19. 19. ADISI 1,4 ASAM KARBOKSILAT α,β-TAK JENUH
  20. 20. SINTESIS ASAM KARBOKSILATAsam Karboksilat dapat disintesis melalui:1. Reaksi RMgX dengan CO2 melalui hidrolisis asam2. Hidrolisis Derivat Asam Karboksilat Oksidasi Alkohol3. Oksidasi Alkena4. Reaksi Haloform (metil keton)5. Oksidasi Alkil Benzen Tersubstitusi1. Reaksi RMgX dengan CO2
  21. 21. 2. Hidrolisis Derivat Asam Karboksilat
  22. 22. 3. Oksidasi
  23. 23. TRANFORMASI DERIVAT ASAM KARBOSILATPrinsip:Reaksi Substitusi Nukleofilik SN2 melalui reaksi Adisi-EliminasiMekanisme reaksi:Reaksi Adisi: pemasukan gugus Nu- pada atom C gugus karboksilReaksi Eliminasi: lepasnya leaving group X-Nu-: H2O, ROH, NH3, RNH2, RCO2-
  24. 24. TRANFORMASI ASAM KARBOSILAT DAN TURUNANNYA
  25. 25. HALIDA ASAMPrinsip:Reaksi Substitusi Nukleofilik SN2 melalui reaksi Adisi-EliminasiMekanisme reaksi:Reaksi Adisi: pemasukan gugus Nu- pada atom C gugus karboksilReaksi Eliminasi: lepasnya leaving group X-Nu-: H2O, ROH, NH3, RNH2, RCO2- dll
  26. 26. HALIDA ASAM1. Hidrolisis atau AlkoholisisHidrolisis menghasilkan asam karboksilat:Mekanisme reaksi:Alkoholisis menghasilkan ester:Mekanisme reaksi:
  27. 27. HALIDA ASAMMekanisme reaksi:2. Pembentukan Amida:
  28. 28. HALIDA ASAM3. ReduksiMekanisme reaksi:
  29. 29. HALIDA ASAM4. Reaksi dengan Organo logamReaksi Grignard: Halida asam + RMgX Alkohol tersierMekanisme reaksi:
  30. 30. HALIDA ASAM4. Reaksi dengan Organo logamHalida asam + Organo kadmium R2Cd KetonSintesis: 2 RMgX + CdCl2 R2Cd + 2 MgCl2Mekanisme reaksi:Halida asam + Organo Tembaga LiCu(CH3)2 Keton
  31. 31. HALIDA ASAM5. Halida asam Anhidrida AsamMekanisme reaksi:6. Halida asam Keton via reaksi Friedel-Craft
  32. 32. HALIDA ASAM7. Halogenasi HαMekanisme reaksi:KESIMPULAN:Halida Asam dapat ditranformasi menjadi:1. Asam karboksilat2. Ester3. Amida4. Anhidrida Asam5. Keton6. Alkohol7. Aldehid
  33. 33. ANHIDRIDA ASAMPrinsip:Reaksi Substitusi Nukleofilik SN2 melalui reaksi Adisi-EliminasiMekanisme reaksi:Reaksi Adisi: pemasukan gugus Nu- pada atom C gugus karboksilReaksi Eliminasi: lepasnya leaving group X-Nu-: H2O, ROH, NH3, RNH2 ,dll
  34. 34. ANHIDRIDA ASAM1. Hidrolisis atau AlkoholisisHidrolisis dalam suasana asam menghasilkan asam karboksilat:
  35. 35. ANHIDRIDA ASAM1. Hidrolisis atau AlkoholisisAlkoholisis menghasilkan ester:
  36. 36. ANHIDRIDA ASAMMekanisme reaksi:2. Pembentukan Amida
  37. 37. SINTESIS ANHIDRIDA ASAM1. Reaksi halida asam + Ion karboksilat2. Pemanasan dwi asam
  38. 38. ESTERSINTESIS ESTER:1. Reaksi asam karboksilat + alkohol2. Reaksi halida asam + alkohol3. Reaksi anhidrida asam + alkohol
  39. 39. ESTERSINTESIS ESTER:4. Reaksi ion karboksilat + alkil halida5. Reaksi asam karboksilat + diazometanMekanisme reaksi
  40. 40. REAKSI KIMIA ESTER1. HIDROLISISMekanisme reaksi (dalam suasana asam)
  41. 41. REAKSI KIMIA ESTER1. HIDROLISISMekanisme reaksi (dalam suasana basa)
  42. 42. REAKSI KIMIA ESTER2. Reaksi dengan pereaksi Grignard:Mekanisme reaksi
  43. 43. REAKSI KIMIA ESTER3. Pembentukan AmidaMekanisme reaksi
  44. 44. REAKSI KIMIA ESTER4. Reduksi[H]: LiAlH4 + H2O; Na + ROH; H2, CuCr2O4. 25C, 200 atm
  45. 45. REAKSI KIMIA ESTER
  46. 46. REAKSI KIMIA ESTER4. Reduksi
  47. 47. REAKSI KIMIA ESTER
  48. 48. LAKTON (ESTER SIKLIK)SINTESIS:1.Reaksi esterifikasi intramolekular:
  49. 49. LAKTON (ESTER SIKLIK)SINTESIS:2. Reaksi Penataan Ulang Baeyer Villager:Mekanisme reaksi:
  50. 50. AMIDAHIDROLISIS DALAM SUASANA ASAM:HIDROLISIS DALAM SUASANA BASA:
  51. 51. SINTESIS AMIDA
  52. 52. NITRIL1. HIDROLISIS DALAM SUASANA ASAM:2. REDUKSI:
  53. 53. SINTESIS NITRIL1. RX + ION NITRIL:2. REAKSI SUBSTITUSI ELEKTROFILIK MELALUI GARAM DIAZONIUM :

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