ORGO Ch. 5 Alcohols Flashcards
What is the alcohol functional group?
Hydroxyl (OH)
What is a phenol?
an alcohol attached to a benzene ring (an aromatic alcohol)
What is a para or p?
when a benzene contains 2 hydroxyls on opposite sides of the ring
What is an ortho or o?
when a benzene contains 2 hydroxyls on adjacent sides of the ring
What is meta or m?
when a benzene contains 2 hydroxyls are separated by a carbon of the ring
Why does alcohol have high melting and boiling points?
they are capable of intermolecular hydrogen bonding. increase hydrogen bonding increases the solubility f alcohols
When can hydrogen bonding occur?
when attached to highly electronegative atoms like N, O, or F
Why can phenols form salts?
they are much more acidic than non-aromatic alcohols because the aromatic ring can delocalize the charge of the conjugate base
What happens when PCC reacts with primary alcohol?
it oxidizes to an aldehyde
Why does the acidity of an alcohol decrease as more alkyl groups are added?
alkyl groups are electron-donating, and thus, the addition of more alkyl groups produces less acidic molecules because it destabilizes the negative charges
What happens when PCC or Na2Cr2O7 reacts with secondary alcohol?
it oxidizes to a ketone
What happens when sodium or potassium dichromate reacts with primary alcohol?
it oxidized to a carboxylic acid
What happens in a Jones oxidation?
chromium trioxide (CrO3) and acetone react with a primary alcohol to produce a carboxylic acid or a secondary alcohol to a ketone
How can hydroxyl become a better leaving group?
it can be protonated to form mesylates and tosylates which are better leaving-group in nucleophilic substitution reactions
What is the functional group of mesylates?
-SO3CH3
