Alcohols Flashcards
phenol
when there is a hydroxide group attached to an aromatic ring
positions relative to the main functional group
ortho-, meta-, para-
physical properties of alcohols
- intermolecular H-bonding
- higher mp
- higher bp
phenols are ____ acidic relative to nonaromatic alcohols.
- much more (resonance stabilization of neg charge)
- form salts with inorganic bases such as NaOH
The hydroxyl hydrogen is…
weakly acidic
alkyl groups…
donate electrons and decrease acidity
more substituted carbocations are more stable
1° alcohol ~~PCC~~>
aldehyde
2° alcohol ~~Na2Cr2O7, H2SO4~~>
ketone
1° alcohol ~~Na2Cr2O7, H2SO4~~>
CA
1° alcohol ~~CrO3, H2SO4, acetone~~>
CA
2° alcohol ~~CrO3, H2SO4, acetone~~>
ketones
mesylates and tosylates
- OH groups are poor LG for nucleophilic sub reactions
- can be reacted to form these
- also protecting reagents
- SO3CH3 and SO3C6H4CH3 respectively
aldehydes and ketones can be reacted w two equivalents of an alcohol or a diol forming…
acetals and ketals
protect from LiAlH4 and other reducing agents
freed using H2O and H+
treatment of phenols w oxidizing agents produces compounds called…
quinones
due to the conjugated ring system, quinones are…
resonance-stabilized electrophiles
not necessarily aromatic
e- receptors in ETC and in photosynthesis and aerobic respiration
