Carboxylic acids + Esters (P2+P3)
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Describe the melting point and boiling point in carboxylic acids
they have hydrogen bonding so have high melting and boiling point.
The longer the carboxylic acid is the…
less soluble it is because the hydrocarbon chain is longer
How are esters formed?
carboxylic acid and alcohol using H2SO4 catalyst forming H2O as a by product reaction is reversible.
What is Hydrolysis?
breaking a bond using water
What is acid catalysed hydrolysis? equation for acid hydrolysis of propylethanoate
esters can be hydrolysed using a H+ catalyst. CH3COOCH2CH2CH3 + H2O <–> CH3COOH + CH3CH2CH2OH
What is base catalysed hydrolysis? equation for base hydrolysis of propylethanoate
esters can be hydrolysed using warm NaOH (base) CH3COOCH2CH2CH3 + NaOH <–> CH3COONa + HOCH2CH2CH3 once the acid is formed it reacts with NaOH to form the salt.
How is a tri-ester formed?
an ester bond between propane-1,2,3-triol and 3 carboxylic acid chains.
General equation for acid hydrolysis of a tri-ester
tri-ester + 3H2O –> propane-1,2,3-triol + carboxylic acid using an acid catalyst under reflux
General equation for base hydrolysis of a tri-ester
tri-ester + 3NaOH –> propane-1,2,3-triol + carboxylic acid salt (SOAP)
General equation to create biodiesel from fatty acids
fatty acids + 3CH3OH <–> 3HC-O-C=O-R + propane-1,2,3-triol
When an acyl chloride is reacted with water what functional group is formed?
Carboxylic acid
When an acyl chloride is reacted with an alcohol what functional group is formed?
Ester
When an acyl chloride is reacted with ammonia what functional group is formed?
Amide
When an acyl chloride is reacted with ammonia what functional group is formed?
Amide
When an acyl chloride is reacted with an amine what functional group is formed?
N-substituted Amide
Describe the mechanism for nucleophilic addition-elimination.
1st arrow from lone pair on nucleophile to C=O 2nd arrow from C=O onto O structure of the intermediate 3rd arrow from O reforming the C=O bond 4th arrow from bond of C-Cl onto the Cl 5th arrow from Nu-H bond onto the Nu.