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MCAT ORGANIC CHEMISTRY: ALCOHOLS

Terms in this set (14)

primary alcohol reacting with PCC
oxidation: production of an aldehyde
primary alcohol with Jones reagent
oxidation: production of a carboxylic acid
secondary alcohol with dichromate salt
oxidation into a ketone
mesylate
a sulfur containing functional group (SO3CH3) derived from methanesulfonic acid: a better leaving group than a hydroxyl: can also act as a protecting group
tosylate
a sulfur/aromatic group that acts as a better leaving group than the hydroxyl group: can also act as a protecting group
protecting groups
usually acetals and ketals: these groups allow for reactions to occur without unwanted reactions with the carbonyl groups of ketones and aldehydes
quinones
result when phenols are reacted with oxidizing agents (chromium salt): usually act as electron acceptors
phylloquinone
vitamin K1 used for photosynthesis and blood clotting
menaquinones
vitamin K2
hydroxyquinones
quinones that have a hydroxy group attached
ubiqionone (coenzyme Q)
a vital electron carrier that associates with complexes I, II, and III in the ETC: reduced form is called ubiquinol: the long tail allows for lipid solubility
PCC
only oxidizing agent that can convert a primary alcohol into an aldehyde
chromium trioxide
Jones: an oxidizing agent used for alcohols
logic behind protecting groups
1. react with diol to make acetal or ketal
2. perform desired reaction
3. react with acid to reform carbonyl and diol
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