Chapter 5 : Alcohols Flashcards
what are alcohols
ROH ; suffix -ol ; prefix hydroxy-
what are phenols
benzene rings with hydroxyl groups
what is ortho position
adjacent carbons on ring
what is meta position
separated by one carbons on ring
what is para position
opposite sides of ring
how do hydrogen bonds affect alcohols
increase boiling and melting points; increase solubility
why are phenols more acidic than alcohols
ring can delocalize charge of conjugate base
how do electron donating groups affect alcohols (alkyl groups)
decrease acidity because they destabilize negative charge
how do electron withdrawing groups affect alcohols (electronegative atoms)
increase acidity because they stabilize negative charge
primary alcohol –> aldehyde
PCC ; weak oxidizing agent
primary alcohol –> carboxylic acid
CrO3 ; Na2Cr2O7 ; K2Cr2O7
secondary alcohol – > ketone
any oxidizing agent
How to make alcohols better LG from nucleophilic substitution reactions
conversion into mesylates or tosylates
what are mesylates
contain –SO3CH3 ; derived from methanesulfonic acid
what are tosylates
contain –SO3C6H4CH3 ; derived from toluenesulfonic acid
how do you protect aldehydes and ketones
conversion into acetals/ketals using two equivalents of alcohol (one equivalent = hemiacetal/ketal) or dialcohol
how do you deprotect aldehydes and ketone
catalytic acid
what are quinones
synthesized through oxidation of phenols ; resonance stabilized electrophiles
what are biologically relevant quinones
vitamin K1 (phylloquinone) and vitamin K2 (menaquinone)
what are hydroxyquinones
oxidation of quinonesw
what is ubiquinone (coenzyme Q)
biologically active quinone that acts as an electron acceptor in complexes I, II, and III of the ETC ; reduced to ubiquinol
