Carboxylic Acid Flashcards
Common name for methanoic acid?
formic acid
Common name for ethanoic acid?
acetic acid
Common name for propanoic acid?
propionic acid
Common name for ethanedioic acid?
oxalic acid
Common name for propanedioic acid?
malonic acid
Common name for butanedioic acid?
succinic acid
Having e- withdrawing substituents _____ acidity.
increases
Having e- donating substituents _______ acidity.
decreases
What is acidity an indicator for?
how easy it is to deprotonate something - more acidic means easier
What accounts for the relatively high acidity of carboxylic acids?
- electron withdrawing oxygen atoms in the functional group
- high stability of the carboxylate anion due to resonance stabilized
What can be oxidized to form a carboxylic acid?
primary alcohols and aldehydes
What are acyl derivatives?
encompass all molecules with a carboxylic acid-derived carbonyl - carboxylic acids, amides, ester, anhydrides
What are lactams?
cyclic amides
What is esterification?
a condensation reaction converted carboxylic acid with alcohol to an ester with water as a side reaction
What are lactones?
cyclic esters
What does reacting two carboxylic acids yield?
anhydride
Carboxylic acid can be reduced to what using LDA?
primary alcohol
LDA and NaBH4 can reduce carboxylic acids? T/F
F - NaBH4 is not strong enough reducing agent
What is decarboxylation?
complete loss of the carboxyl group as carbon dioxide that yields enol/keto
Describe the mechanism of nucleophilic acyl substitution reactions
Nucleophile attacks, opening the carbonyl and forming a tetrahedral intermediate. The carbonyl then reforms, kicking off the leaving group
How is intramolecular cyclic anhydride formation done?
heat
What is the most reactive: anhydrides, esters, and amides
anhydrides
What is the least reactive: anhydrides, esters, and amides
amides
What is induction?
distribution of charge across pi bonds
What is conjugation?
presence of alternating single and multiple bonds
What does reacting an anhyride with ammonia?
amide and carboxylic acid
What does reacting an anhydride with alcohol do?
ester and carboxylic acid
What does reacting an anhydride with water do?
two carboxylic acids
What is transesterification?
alcohols act as nucleophiles and displace the esterifying group on an ester
Under what conditions are amides hydrolyzed?
highly acidic conditions
What does an amide and water yield?
carboxylic acid and ammonia
