26.4 Carboxylic avid derivatives Flashcards
What are the 4 derivatives of carboxylic acids
ester
acyl chlorine
acid anhydride
amide
How do you name an ester
- suffix is ____oate
- the alkyl chain attached to the oxygen atom of COO group is added to the first word in the name
How do you name a acyl chloride
suffix is ____oyl chloride
How is a acid anhydride formed
-removal of water from 2 carboxylic acid molecules
What is esterification
the reaction of an carboxylic acid with a alcohol to form an ester
What are the reagents and conditions required for esterification
-alcohol is warmed with concentrated H2SO4
What is the use of H2SO4 (sulfuric acid) in esterification
acts as a catalyst
What is produced from the reaction of propanoic acid with ethanol
propanoic acid + ethanol = ethyl propanoate + water
What does anhydride mean
with water
Definition of hydrolysis
the chemical breakdown of a compound in the presence of water or in aqueous solution
What are the reagents and conditions required for acid hydrolysis
-ester heated under reflux with dilute aq acid
What is formed during acid hydrolysis
-ester broken down by water with the acid acting as the catalyst
-carboxylic acid and alcohol formed
What is the role of dilute aqueous acid in acid hydrolysis
acts as a catalyst
What are the reagents and conditions required for alkaline hydrolysis
-ester heated under reflux with aq hydroxide ions (or NaOH, KOH etc.)
What is formed from alkaline hydrolysis
-carboxylate ion
-alcohol
What is the equation for reaction of methyl ethanoate and sodium hydroxide
CH3COOCH3 + NaOH = CH3COO-Na+ + CH3OH
How are acyl chlorines prepared
-directly from carboxylic acid by reaction with SOCl2 (thionyl chloride)
What are the precautions for the preparation of acyl chlorines
-volatile so should be carried out in a fume cupboard
-fume cupboard as products are harmful
What are the precautions for the preparation of acyl chlorines
-volatile so should be carried out in a fume cupboard
-fume cupboard as products are harmful
What is the equation for the preparation of acyl chlorine from the reaction of propanoic acid and thionyl chlorine (SOCl2)
CH3CH2COOH + SOCl2 = CH3CH3COCl + SO2(g) + HCl(g)
-SO2 and HCl will evolve off
How do acyl chlorine’s react with nucleophiles
-losing the chlorine ion whilst retaining the C=O double bond
What do acyl chlorine’s react with alcohols to form
Esters
What is the equation for the reaction of acyl chlorine with propane-1-ol
H3CCOCl + CH3CH2CH2OH = H3CCOOCH2CH2CH3 + HCl
What is produced when acyl chlorines react with phenols
phenyl esters
What is produced when acid anhydrides react with phenols
phenyl esters
What are the observations when acyl chlorines react with water
-violent reaction
-evolution of dense steamy hydrogen chloride fumes
-carboxylic acid formed
What is formed when acyl chlorines react with water
carboxylic acid
What is the equation for the reaction of ethanoyl chloride with water
H3CCOCl + H20 = H3CCOOH + HCl
