3.3.9 Carboxylic acids and derivatives Flashcards
Carboxylic acid functional group
-COOH
Ester functional group
O .
ll .
R - C - O - R’
What type of acid are carboxylic acids
Weak acids, they do no fully dissociate in water
Esterification
Alcohol + Carboxylic acid
Acid catalyst
Uses of esters
Perfumes
Plasticisers
Solvents
Food flavourings
Glycerol IUPAC name
propane-1,2,3-triol
What are vegetable oils and fats esters of
Glycerol / propane-1,2,3-triol
Hydrolysis of ester in acidic conditions
Heated under reflux conditions
Produces alcohols and carboxylic acids
Dilute acid catalyst (HCl)
REVERSIBLE
Hydrolysis of ester in alkaline conditions
Heated under reflux conditions
Produces carboxylate salts and alcohols
Dilute alkaline catalyst (NaOH)
ONE WAY
Uses of carboxylate salts
Soap
What is biodiesel
A mixture of methyl esters of long-chain carboxylic acids.
How is biodiesel produced
Vegetable oils + methanol
Strong acid catalyst
Acid anhydride structure
. O
ll
C - R
/
O
\
C - R’
ll
O
Acyl chloride structure
. O
ll
Cl - C - R
What reaction do acid anhydrides and acyl chlorides go through
Nucleophilic addition-elimination
Nucleophiles for electrophilic addition-elimination
Water
Alcohols
Ammonia
Primary amines
Product of nucleophilicaddition elimination of an acid anhydride
. O O
ll AND ll
R- C - Nuc R - C - OH
Industrial advantages of ethanoic anhydride over ethanoyl chloride for manufacturing insulin
- Ethanoic anhydride doesn’t produce dangerous fumes of HCl
- Ethanoic anhydride is not corrosive
- Ethanoic anhydride is not so readily hydrolysed by water
- Ethanoic anhydride is cheaper
