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Alcohols

Alcohols. Biological Activity Nomenclature Preparation Reactions. Some Alcohols. Alcohols are Found in Many Natural Products. Paralytic Shellfish Poisoning. Ethanol: the Beverage. Excess NADH can cause Metabolic Problems. Methanol: Not a Beverage. Synergistic and Metabolic Effects.

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Alcohols

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  1. Alcohols Biological Activity Nomenclature Preparation Reactions

  2. Some Alcohols

  3. Alcohols are Found in Many Natural Products

  4. Paralytic Shellfish Poisoning

  5. Ethanol: the Beverage

  6. Excess NADH can cause Metabolic Problems

  7. Methanol: Not a Beverage

  8. Synergistic and Metabolic Effects • In men, ethanol lowers levels of testosterone (and sperm count) due to lack of enzymes needed for the steroid biosynthesis. • The enzyme CYP2E1, which is responsible for converting acetaminophen into liver toxins, is activated by ethanol. • Ethanol has a caloric value of 7.1Cal/g (fat has a value of 9 Cal/g). • Alcohol can cause a degenerative muscle disease called alcoholic myopathy (3 times more common than cirrhosis).

  9. Synergistic Effects • Women will have higher BAL’s with the consumption of an equal number of drinks due to lower ADH activity and lower % H2O in blood. • Estradiol levels increase in women (and men). This has been associated with higher incidences of heart disease and a change in bone density. • A higher than normal concentration of Cytochrome P-450 enzymes (in the liver) are activated by ethanol creating a potential dependency.

  10. Antitumor Agents • Often functionalized with alcohols • Designed to fit into specific geometic sites on proteins • Hydrogen bonding is crucial for binding • Water solubility is crucial for cell membrane transport

  11. From the Bark of the Pacific Yew TreeTaxol (Paclitaxel)

  12. How Taxol Works • A large number of microtubules are formed at the start of cell division, and as cell division comes to an end, these microtubules are normally broken down into tubulin – a protein responsible for the cell’s structural stability. • Taxol promotes tubulin polymerization then binds to the microtubules and inhibits their depolymerization back into tubulin. • The cell can't divide into daughter cells and therefore the cancer can’t spread.

  13. Tubulin with Taxol bound to one of the Functional DomainsCHIME diagram of tubulin

  14. Taxol Causes Cells’ Tubulin Skeleton to Aggregate in Spindles

  15. May be More Effective than Taxol

  16. DNA Cross-linker

  17. Prevents DNA from Unraveling

  18. Oxidation and Reduction3 hydrocarbon oxidation levels

  19. Oxidation levels of oxygen- halogen- and nitrogen-containing molecules

  20. Acidity of Alcohols • Due to the electronegativity of the O atoms, alcohols are slightly acidic (pKa 16-18). • The anion dervived by the deprotonation of an alcohol is the alkoxide. • Alcohols also react with Na (or K) as water does to give the alkoxide (red-ox):

  21. Withdrawing Groups Enhance Acidity alcohol pKa CH3OH 15.54 CH3CH2OH 16.00 CF3CH2OH 12.43 (CH3)3COH 18.00 (CF3)3COH 5.4

  22. Physical Properties CH3CH2CH3 -42 0.08 i CH3OCH3 -25 1.3 ss CH3CH2OH 78 1.7 vs b.p. oC m D sol. in H2O

  23. Intermolecular H-Bonding

  24. Alcohol Nomenclature

  25. Nomenclature

  26. Who am I?

  27. Preparation of Alcohols • Reduction of ketones and aldehydes • Reduction of esters and carboxylic acids • Hydration of Alkenes • Nucleophilic addition • Grignard reaction • Acetylide addition • Substitution • Epoxide opening

  28. NaBH4 Reduction

  29. Some Examples

  30. Two Alcohol Products Form in Lab

  31. LiAlH4 Reductiona Stronger Reducing Agent

  32. LiAlH4 is a much stronger reducing agent

  33. NaBH4 is More Selective

  34. Oxymercuration HydrationMarkovnikov

  35. Hydroboration HydrationAnti-Markovnikov

  36. Base Catalyzed Ring-Opening of Epoxides

  37. Base Opens Ring from Unhindered Side

  38. Acid Catalyzed Ring-OpeningAqueous and in Alcohol

  39. RegiochemistryRing Opens at More Hindered Site

  40. Different Regiosomers

  41. Propose a Mechanism

  42. 2 SN2 steps

  43. Propose a Mechanism

  44. Nucleophilic addition to Carbonyl CompoundsAcetylides

  45. Organometallic ChemistryGrignard Reaction

  46. Grignard Reagents React With Ketones to form tertiary alcohols

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