26.4 - Carboxylic acid derivatives Flashcards
List 4 carboxylic acid derivatives
Ester
Acyl chloride
Acid anhydride
Amide
What is an esterification (condensation) reaction?
A reaction in which a carboxylic acid reacts with an alcohol to form an ester and water
What conditions are needed for an esterification reaction?
The alcohol is warmed with concentrated sulphuric acid
What are the products of an esterification reaction between propanoic acid + ethanol?
Ethyl propanoate + water
Esters can be hydrolysed by: 1? + 2?
1) Acid (aq)
2) Alkali (aq)
Define hydrolysis
The chemical breakdown of a compound in the presence of water or in aq solution.
What are the products of acid hydrolysis? (ester + water)
Carboxylic acid + alcohol
What conditions are needed for acid hydrolysis?
Heat under reflux with dilute aq acid
What are the products of alkaline hydrolysis?
Carboxylate salt + alcohol
What conditions are needed for alkaline hydrolysis?
Heated under reflux with aq hydroxide ions
What are the products of this alkaline hydrolysis reaction?
methyl ethanoate + NaOH –> ? + ?
Sodium ethanoate + methanol
How do you prepare acyl chlorides?
React carboxylic acid with SOCl2
What condition is needed for the preparation of acyl chlorides?
Fume cupboard
Write an equation for the preparation of propanoyl chloride
propanoic acid + SOCl2 –> propanoyl chloride + SO2 + HCl
Acyl chloride + alcohol –> ? + ?
Ester + HCl
Acyl chloride + phenol –> ? + ?
Ester + HCl
Acyl chloride + H2O –> ? + ?
Carboxylic acid + HCl
What observation would take place when reacting acyl chlorides with water to form carboxylic acids?
Dense, steamy HCl fumes
What is formed when acyl chlorides are reacted with ammonia/amines?
Amides
Do ammonia and amines act as electrophiles or nucleophiles?
Nucleophiles
Products of acyl chlorides + ammonia?
Primary amide + ammonium chloride
Products of acyl chlorides + primary amines?
Secondary amide + other product
Which is more reactive; acyl chlorides or acid anhydrides?
Acyl chlorides
Ethanoic anhydride + phenol –> ? + ?
Phenyl ethanoate + ethanoic acid