CA Flashcards
CA pKa
between 3 and 6
why does CA have a high bp
large IMF
can participate in 2 H bonds
BP inc w molecular weight
CA is one of the most ________ functional groups in OChem and are always ________ groups.
oxidized
terminal
why is CA more reactive than aldehydes and ketones?
additional acidic hydrogen that can participate in reactions
Because of the oxygen and hydrogen of the CA…
can form dimers, pair of molecules held by 2 hydrogen bonds
the carboxylate anion…
is highly stable because of the resonance stabilization between the electroneg atoms due to resonance stabilization
CA are electron_________ meaning
withdrawing
electronegative oxygen atoms meaning that dicarboxylic acids are more acidic than the analogous monocarboxylic acids
what does it mean when a proton is less acidic?
harder to remove.
the hydrogen between a 1,3-dicarbonyl…
is highly acidic bc EWG that oxygens act as
how to form CA
1° alcohol w an oxidizing reagent like:
K2Cr2O7
Na2Cr2O7
CrO3
KMnO4
CA can be reduced back to 1° alcohols by using… which is what kinds of rxn?
- LiAlH4
- nu addition of hydride to carbonyl group
decarboxylation
complete loss of carboxyl group as CO2
when heated, 1,3-dicarboxylic acids and other B-keto acids…
spontaneously decarboxylate
1,3-dicarboxylic acids and B-keto acids decarboxylate in heat by…
losing a carboxyl group and having it replaced w an H
electrophile and nu on same molecule so rxn proceeds through a 6-membered ring transition state, enol initially formed from the destruction but then more stable keto form dominates
saponification
- fatty acid (CA) reacts with NaOH or KOH to form a salt known as soap
- can solvate nonpolar organic compounds in aq solutions bc they contain both nonpolar tail and polar carboxylate head
