University:
Eastern Kentucky University
Course:
CHE 361 | Organic Chemistry I
Academic year:

2020
Views:

308

Pages:

1
Author:

Marin Mason

Organic Chemistry 5: Alcohol Description & Properties Reactions of Alcohols Alcohols: Have the general form ROH and are named with the suffix –ol. If they are NOT the highest priority, they are given the prefix hydroxyPhenols: Benzene ring with –OH groups attached. Named for the relative position of the –OH groups: Primar y Can be oxidized to aldehydes only by pyridinium Alcohols: chlorochromate (PCC); they will be oxidized all the way to carboxylic acids by any stronger oxidizing agents Secondary Can be oxidized to ketones by any common oxidizing agent Alcohols: Alcohols can be converted to mesylates or tosylates to make them better leaving groups for nucleophilic substitution reactions Mesylates: Contain the functional group –SO3CH3 ortho • • • meta para Alcohols can hydrogen bond, raising their boiling and melting points Phenols are more acidic than other alcohols because the aromatic ring can delocalize the charge of the conjugate base Electron-donating groups like alkyl groups decrease acidity because they destabilize negative charges. EWG, such as EN atoms and aromatic rings, increase acidity because they stabilize negative charges Tosylates: Contain the functional group –SO3C6H4CH3 Mesylate Tosylate Aldehydes or ketones can be protected by converting them into acetals or ketals Acetal: A 1° carbon with two –OR groups and an H atom Ketal: A 2° carbon with two –OR groups Reactions of Phenols Quinones: Synthesized through oxidation of phenols. Quinones are resonance-stabilized electrophiles. Vitamin K1 (phylloquinone) and Vitamin K2 (the menaquinones) are examples of biochemically relevant quinones Quinone Hydroxyquinones: Produced by oxidation of quinones, adding a variable number of hydroxyl gruops Ubiquinone: Also called coenzyme Q. Another biologically active quinone that acts as an electron acceptor in Complexes I, II, and III of the electron transport chain. It is reduced to ubiquinol Acetal Ketal Deprotection: The process of converting an acetal or ketal back to a carbonyl by catalytic acid