Alcohols.ppt

Retrosynthesis Some Examples Two Alcohol Products Form in Lab LiAlH4 Reductiona Stronger Reducing Agent LiAlH4 is a much stronger reducing agent NaBH4 is More Selective Oxymercuration HydrationMarkovnikov Hydroboration HydrationAnti-Markovnikov Base Catalyzed Ring-Opening of Epoxides Base Opens Ring from Unhindered Side Acid Catalyzed Ring-OpeningAqueous and in Alcohol RegiochemistryRing Opens at More Hindered Site Different Regiosomers Propose a Mechanism 2 SN2 steps Propose a Mechanism Nucleophilic addition to Carbonyl CompoundsAcetylides Organometallic ChemistryGrignard Reaction Grignard Reagents React With Ketones to form tertiary alcohols Grignard Reagents React With Aldehydes to form secondary alcohols Grignard Reagents React With Formaldehyde to form primary alcohols Grignard Reagents react (twice) with Esters to form 3o Alcohols Grignard Reagents open Epoxides Ring-Opening is Sterically Controlled Grignard Summary Grignard Summary Grignard Reagents are exceptionally strong bases An Effective Use of the BasicityIsotopic Labeling Synthesis Retrosynthetic Analysis 4-Step Synthesis Synthesize Using Only 1,2, or 3-Carbon Reagents 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 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). 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 bloo