carboxylic acids and esters Flashcards
The carboxylic acid are only ____ acids in water and only slightly dissociate, but they are strong enough to displace ____ from carbonates.
weak, carbon dioxide
CH3CO2H(aq) –>< CH3CO2-(aq)+ H+ (aq)
The smaller carboxylic (up to C4) acids dissolve in water in all proportions but after this the solubility
rapidly reduces. They dissolve because they can hydrogen bond to the water molecules.
draw a hydrogen bond from a carboxylic acid to water
describe the strength of carboxylic acids
write an equation for acid + metal (Na) –> salt + hydrogen
CH3CO2H + Na –> CH3CO2-Na+ + H2
write an euation for acid + alkali (NaOH) –> salt + water
CH3CO2H + NaOH –> CH3CO2-Na+ + H2O
write an equation for acid + carbonate (Na2CO3) –> salt + water + CO2
2CH3CO2H + Na2CO3 –> 2CH3CO2-Na+ + H2O + CO2
Carboxylic acids react with ____, in the presence of a strong sulfuric acid catalyst, to form ____ and water.
alcohols , esters
describe esterification using acid anhydrides
acid anhydride –> ester
Reagent: alcohol
Conditions: room temp.
not reversible
describe the hydrolysis of esters with acid reagents
dilute acid (HCl)
conditions: heat under reflux
This reaction is the reverse reaction of ester formation. When an ester is hydrolysed a carboxylic acid and an alcohol are formed.
describe the hydrolysis of esters with sodium hydroxide reagents
dilute sodium hydroxide
conditions: heat under reflux
CH3CH2CO2CH3 + NaOH CH3CH2CO2- Na+ + CH3OH
describe the formation of acyl chloride from a carboxylic acid
CH3COOH + SOCl2 –>
Reaction: carboxylic acid –> acyl chloride
Reagent: SOCl2
Conditions: room tem
CH3COOH + SOCl2 –> CH3COCl + SO2 + HCl
describe the reaction of acycl chlorides with water
Change in functional group: acyl chloride –> carboxylic acid
Reagent: water
Conditions: room temp
Observation: Steamy white fumes of HCl are given off
describe the reaction of acyl chlorides with alcohol
Change in functional group: acyl chloride –> ester
Reagent: alcohol
Conditions: room temp.
Observation: Steamy white fumes of HCl are given off
describe the reaction of acyl chlorides with ammonia
Change in functional group: acyl chloride –> primary amide
Reagent: ammonia
Conditions: room temp.
describe the reaction of acyl chlorides with primary amines
Change in functional group: acyl chloride –> secondary amide
Reagent: primary amine
Conditions: room temp.
describe the reaction of acyl chlorides with phenol
Change in functional group: acyl chloride –> ester
Reagent: phenol
Conditions: room temp.
Observation: Steamy white fumes of HCl are given off
