2. 10.1 Structure and Nomenclature

4. 2. Nomenclature of ether

6. 10.2 Physical properties of alcohols and ethers Alcohols have much higher boiling points than comparable ether or hydrocarbons.

7. 10.3 Important alcohols and ethers Methanol is highly toxic. Ingestion of even small quantities of methanol can cause blindness; large quantities cause death. Methanol poisoning can also occur by inhalation of the vapors or by prolonged exposure to the skin. 10.3A Methanol CH 3 OH

8. 10.3B Ethanol Ethanol can be made by the fermentation of sugars

9. 10.3C Ethylene glycol Ethylene glycol (HOCH 2 CH 2 OH) has a low molecular weight and a high- boiling point is miscible with water. It is an ideal automobile antifreeze.

10. 10.3D Diethyl Ether Diethyl ether is a very low-boiling, highly flammable liquid. Care should always be taken when diethyl ether is used in the laboratory, because open flames or sparks from light switches can cause explosive combustion of mixtures of diethyl ether and air. You have to add FeSO 4 to remove a hydroperoxide

11. 10.4 Synthesis of alcohols from alkenes 10.4A Hydration of alkenes

12. 10.5 Alcohols from alkenes through oxymercuration- Demercuration

14. A mechanism of addition of Hg(OAc) 2

15. 10.6 Hydroboration ( 硼氢化反 应 ): Synthesis of organoboranes ( 有机硼的合成）

16. BH 3 is a Lewis acid (because the boron has only six electrons in its valence shell). It accepts an electron pair from the oxygen atom of THF

17. 10.6A Mechanism of hydroboration

18. 10.6B The stereochemistry of hydroboration 硼氢化反应的特点； 1. 顺式加成。 2. 反马加成

19. 10.7 Alcohols from alkenes through hydroboration- oxidation

21. 10.8 Reaction of alcohols

22. The Hydroxyl group (OH) is replaced by other groups (Nu: - )

24. 10.10 Conversion of alcohols into mesylates （甲基磺酸酯） and tosylates （苯磺酸酯）

27. 10.11 Mesylates and tosylates in S N 2 reaction

28. 10.12 Alkyl phosphates ( 烷基磷酸酯） Alcohols (ROH) react with phosphoric acid (H 3 PO 4 ) to yield alkyl phosphates

29. 10.13 Conversion of alcohols into alkyl halides Alcohols react with a variety of reagents to yield alkyl halides. The most commonly used reagents are hydrogen halides (HCl, HBr, or HI), Phosporous tribromide (PBr 3 ), and thionly chloride (SOCl 2 ).

31. 10.14 Alkyl halides from the reactions of alcohols with hydrogen halides

32. 10.14A Mechanisms of the reactions of alcohols with HX 酸 (H + ) 和 Lewis acid (ZnCl 2 ) 促进此反应。

33. 10.15 Alkyl halides from the reactions of alcohols with PBr 3 or SOCl 2

35. 10.16 Synthesis of ether 醚的合 成 10.16A Ethers by intermolecular dehydration of alcohols ( 醇的分子间脱水制 醚）

36. 10.16B The Williamson synthesis of ethers ( 醚的威廉 姆孙合成） An important route to unsymmetrical ethers is a nucleophilic substitution reaction known as the Williamson synthesis.

37. How to synthesis of ethyl propyl ether (CH 3 CH 2 CH 2 OCH 2 CH 3 )

38. 10.16C tert-Butyl ethers by alkylation of alcohols

39. 10.16D Trimethylsilyl ethers. Silylation （三甲硅醚 --- 甲硅烷基化作用） A hydroxyl group can also be protected in neutral or basic solutions by converting it a trimethylsily ether group, -OSi(CH 3 ) 3. This reaction, called silylation, is done by allowing the alcohol to react with chlorotrimethylsilane in the presence of a tertiary amine

41. 10.17 Reactions of ethers Heating dialkyl ethers with very strong acids (HI, HBr, and H 2 SO 4 ) cause them to undergo reactions in which the carbon- oxygen bond breaks. Diethyl ether, for example, react with hot concentrated hydrobromic acid to give two molar equivalents of ethyl bromide

42. The mechanism for this reaction

43. 10.18 Epoxides 环氧化物 Epoxides (Oxirane) are cyclic ethers with three-membered rings.

44. Synthesis of epoxides

46. 10.19 Reactions of epoxides The highly strained three-membered ring in molecules of epoxides makes them much more reactive toward nucleophilic substitution than other ethers. Acid-Catalyzed Ring Opening;

47. Based-Catalyzed Ring Opening;

48. If the epoxide is unsymmetrical, in base-catalyzed ring opening attack by the alkoxide ion occurs primarily at the less substituted carbon atom.

49. In the acid-catalyzed ring opening of an unsymmetrical epoxide the nucleophile attacks primarily at the more substituted carbon atom.

50. 10.20 Anti hydroxylation of alkenes via epoxides ( 烯烃经环氧化物的反式 - 羟基化）

51. Mechanism of this reaction;

54. 10.22 Crown Ethers; （冠醚） 1. Phase-Transfer catalysis (PTC) ( 相转移 催化） No catalyst, needed long time to finish this reaction. Add Q + X - (PTC) to speed up reaction.

55. Fig. Phase-transfer catalysis of the S N 2 reaction between sodium cyanide and an alkyl halide.

57. 10.22A Crown ethers Compounds called crown ethers are also phase-transfer catalysts and are able to transport ionic compounds into an organic phase. 提高了 KMnO 4 的氧化能力和提高了亲核试剂 KCN 的亲核能力。