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Carboxylic Derivatives (Esters, Acyl Chlorides and Fats) Summary - Unit A2 1 - Periodic Trends and Further Organic, Physical and Inorganic Chemistry £5.49
Forming esters - alcohol and carboxylic acid Hydrolysis of esters in acid conditions
Carboxylic acid + alcohol Ester + water Reversible reaction so reaches equilibrium
O O
H2SO4 catalyst O Ester + water Carboxylic acid + alcohol
+ Heat + E.g.
HO 11
O
H H
Propyl butanoate + water Butanoic acid + propanol
OH
Ethanoic acid Propan-1-ol Propyl ethanoate Water Conditions - dilute HCl catalyst (doesn’t affect
equilibrium)
Naming esters Hydrolysis of esters in alkaline conditions
Carboxyl group has higher priority than Esters Ester + alkali Salt + alcohol
alcohol group. Alkali is consumed in reaction
We treat the part of the ester that has -COO- functional group Non-reversible reaction, no equilibrium.
come from the carboxylic acid as the main O Physical properties of esters
carbon chain. (C=O bond) Solubility decreases as the length of the chain
Must be a
The alcohol is then converted to an alkyl increases, as hydrogen bonds between the polar
carbon atom
name and used as a prefix. C group on the ester and water decrease as the
R
The name of an ester reflects alcohol first, 2 non-polar hydrocarbon chain increases.
acid second. R O Intermolecular forces in esters is mostly Van der
1
Waals forces of attraction with some permanent
Forming esters - alcohol and acyl chloride
dipole-dipole between the polar C=O. This means it
The Cl of the acyl chloride reacts with the H from the OH group in the has a higher boiling point than alkanes with a
alcohol to form HCl. (Acyl = carbonyl group derived from CA.) similar RMM, but lower than carboxylic acids with
E.g. a similar RMM.
CH3 CH2OH + CH3CH2 COCl CH3CH2COOCH2 CH3 + HCl As the length of the carbon chain increases, so
does esters boiling point due to more electrons
The reaction of acyl chloride with alcohol produces a higher yield of the
therefore more induced dipoles therefore more Van
ester (without the conc. acid or heating) as the gaseous HCl is removed from
der Waals forces of attraction.
the equilibrium of the mixture, which promotes the formation of the ester.
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