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MCAT Org. Chem Ch. 5

QuestionAnswer
Alcohols Have the general form, ROH, and are named with the suffix, -ol. If they are not the highest priority present, they are given the prefix, hydroxy-
Phenols Benzene rings with hydroxyl groups. They are named for the relative positions of the hydroxyl groups. (ortho, meta, para)
Ortho- Adjacent carbons
Meta- Separated by one carbon
Para- On opposite sides of the ring
Properties Of Alcohol They can hydrogen bond, raise their boiling and melting points relative to corresponding alkanes.
Hydrogen Bonding And Solubility Of Alcohols H-bonding increases the solubility of alcohols.
Reason Why Phenols Are More Acidic They are more acidic because the aromatic ring can delocalize the charge of the conjugate base.
Reason Why Electron-donating Groups (like Alkyl Groups) Decrease Acidity Because they destabilize negative charges.
Reason Why Electron-withdrawing Groups (ex: Electronegative Atoms and Aromatic Rings) Increase Acidity Because they stabilize negative charges.
Pyridnium Chlorochromate (PCC) Only substance used to oxidize primary alcohols to aldehydes. Otherwise, the primary alcohols will be oxidized all the way to carboxylic acids by stronger oxidizing agents.
How Secondary Alcohols Can Be Oxidized To Ketones This can be done by any common oxidizing agent.
Why Alcohols Are Converted To Mesylates Or Tosylates To make them better leaving groups for nucleophilic substitution reactions
Mesylates Contain the functional group, -SO3CH3, which is derived from methanesulfonic acid.
Tosylates Contain the functional group, -SO3C6H4CH3, which is derived from toluenesulfonic acid.
How Aldehydes or Ketones Can Be Protected Convert them into acetals or ketals
Process Of How Aldehydes Or Ketones Can Be Protected 1. Two equiv's of alcohol or a dialcohol are reacted with carbonyl to form the acetal or ketal
Acetal Primary carbon with two -OR groups and a hydrogen atom
Ketal A secondary carbon with two -OR groups.
Note About Other Functional Groups In The Aldehyde / Ketone Compound During Acetal or Ketal Rxn They can be reacted without having effects on the newly formed acetal or ketal
Deprotection Process of converting an acetal or ketal back to a carbonyl by catalytic acid
Quinones Synthesized through oxidation of phenols. They are resonance-stabilized electrophiles.
Phylloquinone Vitamin K1, an example of a biochemically relevant quinone
Menaquinone Vitamin K2, an example of a biochemically relevant quinone
Hydroxyquinones Produced by oxidation of quinones, adding a variable number of hydroxyl groups
Ubiquinone (Coenzyme Q) A biologically active quinone that acts an electron acceptor in Complexes I, II, and III of the electron transport chain.
Ubiquinol Reduced form of Ubiquinone.
Created by: SamB91