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Alkohol dan Eter

Alkohol dan Eter. Ikatan tunggal Karbon ke Oksigen. Tata Nama: AlKohol. OH ditunjukkan oleh akhiran ol Rantai induk adalah rantai terpanjang yang mengandung C-OH Karbon dinomori dari ujung rantai yang terdekat –OH. Contoh. Tata Nama: Eter. Eter sederhana :

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Alkohol dan Eter

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  1. Alkohol dan Eter Ikatan tunggal Karbon ke Oksigen

  2. Tata Nama: AlKohol • OH ditunjukkan oleh akhiran ol • Rantai induk adalah rantai terpanjang yang mengandung C-OH • Karbon dinomori dari ujung rantai yang terdekat –OH

  3. Contoh

  4. Tata Nama: Eter • Eter sederhana : nama dua gugus karbon sebagai substituen, diikuti dengan eter • Sistematik: nama sebagai alkoksi alkana

  5. Contoh

  6. Gugus Fungsional Alkohol Tiga lokasi dimana kimia bisa terjadi • Lokasi kaya elektron? • Lokasi miskin elektron?

  7. The Ether Functional Group Same as Alcohols, but no O-H

  8. Reactions of the C-O Bond Does this happen? NO. The C-O is inert toward heterolytic cleavage. Why? OH--is too basic to be a leaving group.

  9. Ikatan C-O putus pada kondisi asam Substitution Elimination

  10. Kenapa ikatan C-O putus pada kondisi asam? Alkohol adalah basa lemah, bereaksi dengan asam kuat (Bronsted or Lewis).

  11. C-O dari alkohol terprotonasi bisa putus • Suatu reaksi substitusi nukleofilik • Air sebagai gugus lepas • SN2 jika primer uncrowded • SN1 (seperti terlihat)

  12. Ether Chemistry is C-O Chemistry --Just Like Alcohol C-O Chemistry

  13. Identical Mechanisms, Too. Protonation of the O, then Nucleophilic Substitution

  14. Predicting the Products • Ether cleavage is not usually selective; both sets of cleavage products are to be expected. In methyl ethers, the X preferentially attacks the methyl group. In excess HX, both C-O are cleaved, producing water and two C-X bonds. In phenyl ethers, the benzene ring is not attacked, even in excess HX.

  15. Ether Cleavage Reactions

  16. Alcohol Reactions Not Involving C-O Cleavage Electron-rich oxygen The O-H

  17. Reactions of the O-H Water has the same functional group The H is electron-poor. Are alcohols acids? Learn from water’s chemistry

  18. The Acidity of Alcohols • H-O-H pKa = 15.7 • R-O-H pKa = 15 to 16 • R-NH2 pKa = 34

  19. Reaction with active metals

  20. Other Ways to Convert the OH to a Good Leaving Group: Halides

  21. Reactions Using the Lone Electron Pairs of Oxygen Base? Nucleophile?

  22. Alcohols and Ethers are Weakly Basic • They are protonated in strong acids. All oxygenated organic compounds are protonated by strong acids

  23. Alcohols are Nucleophiles …but not very strong ones. There is no alkoxide (RO-) in alcohol!!

  24. Conversion to Sulfonates Nucleophilic Substitution by Alcohol at Sulfur!!

  25. Sulfonate is a Good Leaving Group As good as or better than bromide

  26. Oxidation of Alcohols:Preparation of C=O bonds

  27. Three Ways to Make the Alcohol Carbon More Electrophilic

  28. DEHIDRASI ALKOHOL

  29. Alcohols in Synthesis

  30. Reaksi Pembukaan cincin Epoksida • The three-membered ring of epoxides is highly strained and undergoes ring-opening reactions with a variety of nucleophiles, as shown below.

  31. Reaksi berkatalisis asam

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