Chapter 8: Carboxylic Acids Flashcards
carbonyl group
hydroxyl group
ketone structure
ether structure
aldehyde structure
carboxylic acid structure
note: carboxylic acids are always TERMINAL groups
acyl group
beta-dicarboxylic acids
2 carboxylic acids separated by a single carbon
the alpha hydrogens are very acidic (they leave easily), producing a carbanion which is resonance stabilized
carboxylic acid synthesis reactions
carboxylic acids can be synthesized in multiple ways, such as:
oxidation of aldehydes and primary alcohols
nucleophilic acyl substitution reactions
a nucleophile forms a new bond with the carbonyl carbon of an acyl group; a bond is broken between the carbonyl carbon and a leaving group
_____ (weak/strong) baes make good leaving groups
weak
amide formation
the incoming nucleophile is ammonia (NH3) or an amine; carboxylic acids can are converted into amides
a nucleophilic acyl substitution
amide structure
lactams
cyclic amides
ester structure
esterification
an alcohol and an acid react to produce an ester and water
a nucleophilic acyl substitution reaction
what type of reaction is esterification?
a condensation reaction: 2 molecules combine to form a single molecule, with a loss of water
lactones
cyclic esters
anhydride structure
anhydride formation
formed by the condensation of 2 carboxylic acids
a nucleophilic acyl substitution reaction
reduction of carboxylic acids to primary alcohols
via nucleophilic addition of hydride (H-) to the carbonyl group
requires a strong reducing agent such as LiAlH4
decarboxylation reactions
a chemical reaction that removes CO2 from a carboxyl group, leaving behind a hydrogen
saponification reactions
long chain carboxylic acids (fatty acids) react with sodium or potassium hydroxide to form a salt (SOAP)
carboxylic acid salt (soap) structure
