1. Alcohols < < Nomenclature < < Properties < < Preparation < < Reactions < < Spectroscopy

2. Alcohol Nomenclature IUPACCommonCarbinol

3. Preparation Reactions  Reduction of carbonyl compounds  Hydration of Alkenes  Grignard reactions

4. Reduction of Carbonyl Compounds Reduction of Aldehydes/ketones Reduction of Aldehydes/ketones Reduction of Carboxylic acids/Esters Reduction of Carboxylic acids/Esters

5. Reduction of Aldehydes/Ketones Hydrogenation

6. Hydride Reductions

7. Reduction of Carboxylic Acids and Esters Lithium Aluminum Hydride Reduction

8. Hydration of Alkenes   Acid catalyzed Hydration   Oxymercuration-Demercuration   Hydroboration-Oxidation

9. Acid-Catalyzed Hydration of Alkenes  Markovnikov addition  Formation of most stable carbocation  Shifts/rearrangements possible

10. Hydration of Alkenes via Oxymercuration/Demercuration Y Markovnikov addition Y Typically no shifts/rearrangements Y Mercurinium ion involvement

11. Hydroboration-Oxidation of Alkenes  Anti-Markovnikov addition  No shifts/rearrangements  Syn addition

12. Grignard Addition Reactions Addition to Aldehydes/Ketones Addition to Aldehydes/Ketones Addition to Esters Addition to Esters Addition to Epoxides Addition to Epoxides

13. Grignard Additions to Aldehydes/Ketones Formation of primary, secondary, and tertiary alcohols

14. Grignard Additions to Esters Formation of secondary and tertiary alcohols

15. Grignard Addition to Epoxides

16. Typical Alcohol Reactions  Salt formation  Dehydration  Oxidation  Alkyl halide formation  Ester formation  Ether synthesis  Periodic acid cleavage of glycols  Haloform reaction of methyl carbinols  THP acetal formation

17. Conversion of Alcohols to Salts Reaction with Active Metals

18. Dehydration of Alcohols

19. Oxidation of Alcohols

20. Alcohol Conversion to Alkyl Halides  Reaction with Hydrogen halides  Reaction with Thionyl chloride  Reaction with Phosphorus trihalides or pentahalides

21. Hydrogen Halide Conversion of Alcohols to Alkyl Halides

22. Conversion of Alcohols to Alkyl Chlorides via Thionyl Chloride

23. Conversion of Alcohols to Alkyl Halides via Phosphorus Halides

24. Ester Formation from Alcohols

25. Periodic Acid Cleavage of Glycols

26. Haloform Reaction Methyl carbinol cleavage to give Carboxylic acids and Haloform

27. Disguising an Alcohol Creating a tetrahydropyranyl acetal

28. Spectroscopic Characteristics of Alcohols  Infrared  Pmr  Cmr

29. EthersEthers H Nomenclature H Properties H Preparation H Reactions H Nomenclature H Properties H Preparation H Reactions

30. Ether Nomenclature

31. Preparation of Ethers Dehydration of Alcohols Dehydration of Alcohols Williamson synthesis Williamson synthesis Alkoxymercuration- Demercuration Alkoxymercuration- Demercuration Peroxyacid Epoxidation of Alkenes

32. Ether Formation via Acid Catalyzed Dehydration of Alcohols

33. Williamson Synthesis of Ethers Bimolecular Substitution by Alkoxide on a suitable substrate

34. Alkoxymercuration- Demercuration of Alkenes Y Markovnikov Addition Y Typically no rearrangements/shifts Y Mercurinium ion involvement

35. Epoxidation of Alkenes Prilezhaev reaction

36. Ether Reactions Y HX Cleavage Y Epoxide Ring Opening

37. HX Cleavage of Ethers Unimolecular or Bimolecular Cleavage Pathways

38. Epoxide Ring Opening Unimolecular or Bimolecular