Chapter 8- Carboxylic Acids Flashcards
one of the most reactive organic molecules encountered on test day
carboxylic acids with both carbonyl and hydroxyl groups.
where are carboxylic acids found
in amino acids
also soap, oil, preservatives, skin care products, and clothing
pKa value of most carboxylic acids and alcohols
carboxylic acids: between 3 and 6
alcohols: ~17
* note: lower pKa = stronger acid
if there is only one carbon for a carboxylic acid what is it called
formic acid
formic acid
carboxylic acid with only one carbon atom in total
carboxylic acids physical properties
- polar
- can form hydrogen bonds
- very acidic (due to resonance stabilization and can be enhanced by the addition of electronegative groups or a greater ability to delocalize charge)
- highest boiling and melting points (more than alcohols, ketones, and aldehydes)
dimer
pairs of molecules connected by two hydrogen bonds. carboxylic acids usually form these.
two examples of electron-withdrawing groups and two examples of electron-donating groups
EWG- NO2 and halides (increase acidity)
EDG- NH2 and OCH3 (decrease acidity)
main oxidizing agent to synthesize carboxylic acids
KMnO4
what makes a good leaving group
weak bases. favored reaction in acidic or basic conditions.
if a nucleophilic amine reacts with a carboxylic acid in either a base or an acid what happens
an amide is formed
lactams
cyclic amides (carboxylic acid and amine)
ester
hybrid between carboxylic acid and ether (ROR’), can be made by reacting carboxylic acids with alcohols under acidic conditions
essentially a carboxylic acid with an oxygen somewhere in the chain as well (typically alpha position).
what happens when a carboxylic acid reacts with an alcohol under acidic conditions
esterfication (type of condensation reaction)
lactone
esters that are cyclic
