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  1. 1. Alkohol dan Eter Ikatan tunggal Karbon ke Oksigen
  2. 2. Tata Nama: AlKohol OH ditunjukkan oleh akhiran ol Rantai induk adalah rantai terpanjang yang mengandung C-OH Karbon di K b dinomori dari ujung rantai yang id i j t i terdekat –OH
  3. 3. Contoh C h OH OH H3C CH2 CH CH2 CH CH3 CH3 F 5-methyl-3-hexanol CH3 (1R,3S,4S)3-fluoro-4-methylcyclohexanol, or (1R 3S 4S)3 fl 4 th l l h l (1R,3S,4S)3-fluoro-4-methyl-1-cyclohexanol HO OH hex-5-en-2-ol or 3-(1-methylpropyl)-2-heptanol 3 (1 methylpropyl) 2 heptanol 5-hexen-2-ol (Note that the OH takes precedence over the pi bond in detemining the numbering.)
  4. 4. Tata Nama: Eter Eter sederhana : nama dua gugus karbon sebagai substituen, diikuti dengan eter Sistematik: Si t tik nama sebagai alkoksi alkana
  5. 5. Contoh C h CH3 CH2 O CH2 CH3 diethyl dieth l ether or ethyl ether (If both alkyl groups are the O same, same the "di" is often not used ) di used.) phenoxycyclopentane or O cyclopentyloxybenzene CH2-CH3 5-ethoxy-2-methylheptane
  6. 6. Gugus Fungsional Alkohol G i l lk h l Tiga lokasi dimana reaksi kimia bisa terjadi .. .. O H •Lokasi kaya elektron? •Lokasi miskin elektron? Lokasi
  7. 7. The Eth F Th Ether Functional Group ti lG Same as Alcohols but no O-H Alcohols, O C C
  8. 8. Reaksi pada ikatan C O C-O Does this happen? pp .. .. - O Nuc: + H Nuc + OH The C-O is inert toward heterolytic cleavage CO cleavage. Why? OH- terlalu basa untuk menjadi gugus lepas
  9. 9. Ikatan C-O putus pada kondisi asam . . .. O Br + H + H + Br + H2O Substitution OH + H H + H2O Elimination
  10. 10. Kenapa ikatan C-O putus pada kondisi k di i asam?? H H O: .. H OSO3H O + H H H .. + HSO4- H H O: .. H OSO3H O + H .. + HSO4- Alkohol adalah basa lemah, bereaksi dengan asam lemah kuat (Bronsted or Lewis).
  11. 11. C-O dari alkohol terprotonasi bisa putus .. .. H O .. + - H + HA O H + A H .. + O H + + H2O slow + _ + A A •Suatu reaksi substitusi nukleofilik •Air sebagai gugus lepas •SN2 jika primer uncrowded •SN1 (seperti terlihat)
  12. 12. Substitution of the Hydroxyl Hydrogen
  13. 13. Ether Chemistry is C-O Chemistry CO --Just Like Alcohol C-O Chemistry O H X H + H-X + O H H O X + H-X + O
  14. 14. Identical Mechanisms, Too. Protonation of the O, then Nucleophilic Substitution H H-X + H O O X H X H + O H H-X H H + X O O X O +
  15. 15. Prediksi Produk Pemutusan Ether tidak selalu selektif; kedua set produk pemutusan diharapkan. p p p Dalam metil eter, X lebih menyukai menyerang gugus metil. Dalam HX berlebih, kedua C-O diputus, menghasilkan air dan dua ikatan C-X. Dalam fenil eter, cincin benzena tidak diserang, walaupun dalam HX berlebih.
  16. 16. Ether Cl Eth Cleavage Reactions R ti CH3 CH O CH2 CH3 + H-I CH3 excess O + H-I HI excess CH3 O +H-I one equivalent O + H-I excess + H-I O excess
  17. 17. Reaksi Alkohol yang tidak melibatkan pemutusan C-O Electron-rich oxygen The O-H
  18. 18. Reactions of the O-H Water has the same functional group .. .. O H + :Base Atom H adalah miskin elektron Are alcohols acids? Learn from water s chemistry water’s
  19. 19. Keasaman Alkohol H-O-H pKa = 15.7 ROH R-O-H pKa = 15 to 16 R-NH2 pKa = 34 CH3 CH2 OH + HO CH3 CH2 O + H2O CH3 CH2 OH + H2N CH3 CH2 O + NH3
  20. 20. Reaksi dengan logam aktif R O H + M. R O M +2 H2 M can be Na or K K OH OK Na OH ONa ON
  21. 21. Other Ways to Convert the OH to a Good Leaving Group: Halides OH + PBr3 OH + SOC SOCl2
  22. 22. Reaksi menggunakan pasangan elektron bebas dari oksigen Basa? Nucleophile?
  23. 23. Alcohols a d Ethers a e o o s and e s are Weakly Basic They are protonated in strong acids. O H H + H O + H2SO4 H O O+ CH3 CH3 + H2SO4 All oxygenated organic compounds are protonated b strong acids t t d by t id
  24. 24. Alcohols are Nucleophiles …but not very strong ones. X + + C R O C R O C R O C H H With methyl and primart halides, this y p probably happens by an SN2 mechanism Note that the nucleophile is NOT alkoxide! Like water, alcohols are not strong acids, so there is no R O- present The nucleophile acids R-O present. is the whole alcohol molecule., There is no alkoxide (RO-) in alcohol!!
  25. 25. Conversion to Sulfonates Nucleophilic Substitution by Alcohol at Sulfur!! SO2Cl OH O O SO2 + OH O Ts + Ts-Cl H OH H OTs CH3 CH3 H3C + Ts-Cl H3C CH3 CH3
  26. 26. Sulfonate is a Good Leaving S lf i G dL i Group p As good as or better than bromide OTs S-CH3 + Na SCH Na-SCH3 + Ts T O CH3 CH3 H OTs I H H3C CH2 CH3 + NaI H3C CH2 CH3 + Ts O
  27. 27. Oksidasi alkohol Pembuatan ikatan C=O OH O H oxidize OH HCrO3 CH3CH2CH2 C CH3 C H CH2-OH CrO3 pyridine idi CH2-OH HCrO3 CO
  28. 28. Three Ways to Make the Alcohol Carbon More Electrophilic OH X Convert to a better leaving group OH OTs H OH O Oxidize
  29. 29. Elimination Reactions of Alcohols
  30. 30. Step (1) The alcohol is protonated by the oxonium ion from the acid solution solution. Step (2) Heterolytic C-O bond fission occurs to give the carbocation and water. i h b i d In Step (3) the carbocation is 'deprotonated' to give the alkene and oxonium ion. The double bond is completed from the C-H bonding pair of electrons 'left' as the proton is removed.
  31. 31. Alkohol dalam Sintesis o o da a S es s Nu OTs Nu: Nu TsCl X MgX Mg OH HX, or SOCl2 or PBr3 Strong base H+, heat oxidize O etc.
  32. 32. The three-membered ring of epoxides is highly strained and undergoes ring-opening reactions with a variety of nucleophiles, as shown below.