Chapter 5- Alcohols Flashcards
hydroxyl group
-OH (can be on protic solvents)
phenols
aromatic alcohols (the H of the hydroxy group is more acidic due to the ring its attached to) higher Ka and lower pKa = more acidic.
one of the most prominent properties of alcohols
capable of intermolecular hydrogen bonding, resulting in significantly higher melting and boiling points.
what does hydrogen bonding do to physical properties
causes increased melting points, boiling points, and solubility in water.
main reactions seen for alcohols on MCAT
oxidation
preparation of mesylates and tosylates
protection of carbonyls by alcohols
what happens when primary alcohols are oxidized by PCC
forms aldehyde
what happens when secondary alcohols are oxidized by PCC (or any stronger oxidizing agent)
forms ketone
what happens when a primary alcohol gets oxidized by a strong oxidizing agent that ISNT PCC
forms carboxylic acid
strong oxidizing agents (Na2Cr2O7 or K2Cr2O7)
what happens when an alcohol is oxidized by a VERY strong oxidizing agent
Jones oxidation using CrO3, H2SO4 and acetone.
primary alcohols form carboxylic acid
secondary alcohols form ketones
what is the purpose of a mesylate and a tosylate
hydroxyl (OH) groups are poor leaving groups so they can turn into these to become better leaving groups for nucleophilic substitution reactions
mesylate
-SO3CH3 (derived from methanesulfonic acid)
prepared in presence of base
tosylate
-SO3C6H4CH3 (derived from toluenesulfonic acid)
reactions with phenols and oxidizing agents
forms quinones (in K2)
what is a quinone and what can it be oxidized to
quionone forms when a phenol is oxidized.
a quionone can be oxidized to a hydroxyquinone (can be used in synthesis of medication)
ubiquinone
aka. coenzyme Q. one example of a biologically active quinone. vital electron carrier associated with complexes I, II, III of ETC.
