Summary
Summary Acylation (Unit 3.3.9)
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Notes on Acylation from Year 13/A2 Organic Chemistry (AQA)
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Acyl Chlorides & Acid AnhydridesAcyl chlorides are derivatives of carboxylic acids by the
substitution of the -OH group for a chlorine atom. The functional
group for acyl chlorides is COCl, with all names ending in -oyl
chloride.
Acid anhydrides are also derivatives of carboxylic acids formed by
substitution of the -OH group by an alkanoate. The functional
group for acid anhydrides is R(CO)O(CO)R, with all names ending in
-oic anhydride.
E.g.
Propanoyl Chloride Propanoic Anhydride
Nucleophilic Addition - Elimination
Due to the difference in electronegativity bet ween the oxygen
atoms and the carbon atoms, there is a dipole present. The carbon
is partially positive so it attracts nucleophiles readily.
When an acyl chloride reacts with a nucleophile it substitutes its
Cl and misty fumes of HCl are given off. Acid anyhydrides produce
a similar reaction as acyl chlorides but a carboxylic acid is formed
instead of HCl.
Different nucleophiles produce different products in nucleophilic
addition - Elimination reactions.
, Reactions Of Acyl Chlorides & Acid Anhydrides With Water
Acyl chlorides & acid anhydrides react with cold water to form
carboxylic acids.
E.g. Propanoyl Chloride To Form Propanoic Acid
*Misty fumes of HCl are also produced in this reaction.
E.g. Ethanoic Anhydride To Form 2 Molecules Of Ethanoic Acid
Reactions Of Acyl Chlorides & Acid Anhydrides With
Alcohols
Acyl chlorides & acid anhydrides react with alcohols at room
temperature to form esters as the product.
E.g. Ethanoyl Chloride To Form Methyl Ethanoate
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