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alkohol-eter
Alcohols and ethers contain the C-O functional group. Alcohols have an O-H bond while ethers do not. The C-O bond in alcohols and ethers is inert to heterolytic cleavage but can undergo substitution reactions under acidic conditions via protonation of the oxygen. Ether chemistry follows similar mechanisms to alcohol chemistry involving C-O bond cleavage and substitution. Alcohols can act as weak acids via protonation of the O-H bond or as nucleophiles. Common reactions of alcohols include oxidation to form carbonyl compounds, conversion of the O-H to a better leaving group followed by substitution, and elimination reactions to form alkenes
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alkohol-eter
- 1. Alkohol dan Eter Ikatantunggal Karbon ke Oksigen
- 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
- 4. 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.)
- 5. Tata Nama: Eter Eter sederhana : nama dua gugus karbon sebagai substituen, diikuti dengan eter Sistematik: Si t tik nama sebagai alkoksi alkana
- 6. 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
- 9. 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
- 10. The Eth F ThEther Functional Group ti lG Same as Alcohols but no O-H Alcohols, O C C
- 11. Reaksi pada ikatanC 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
- 12. Ikatan C-O putuspada kondisi asam . . .. O Br + H + H + Br + H2O Substitution OH + H H + H2O Elimination
- 13. Kenapa ikatan C-Oputus 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).
- 14. C-O dari alkoholterprotonasi 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)
- 15. Substitution of theHydroxyl Hydrogen
- 16. Ether Chemistry isC-O Chemistry CO --Just Like Alcohol C-O Chemistry O H X H + H-X + O H H O X + H-X + O
- 17. Identical Mechanisms, Too. Protonationof 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 +
- 18. Prediksi Produk PemutusanEther 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.
- 19. 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
- 20. Reaksi Alkohol yangtidak melibatkan pemutusan C-O Electron-rich oxygen The O-H
- 21. Reactions of theO-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
- 22. 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
- 23. Reaksi dengan logamaktif R O H + M. R O M +2 H2 M can be Na or K K OH OK Na OH ONa ON
- 24. Other Ways toConvert the OH to a Good Leaving Group: Halides OH + PBr3 OH + SOC SOCl2
- 25. Reaksi menggunakan pasangan elektronbebas dari oksigen Basa? Nucleophile?
- 26. Alcohols a dEthers 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
- 27. 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!!
- 28. Conversion to Sulfonates NucleophilicSubstitution 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
- 29. Sulfonate is aGood 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
- 30. 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
- 31. Three Ways toMake the Alcohol Carbon More Electrophilic OH X Convert to a better leaving group OH OTs H OH O Oxidize
- 33. Elimination Reactions ofAlcohols
- 35. Step (1) Thealcohol 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.
- 37. 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.
- 38. The three-membered ringof epoxides is highly strained and undergoes ring-opening reactions with a variety of nucleophiles, as shown below.