Acylation
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What are acid anhydrides formed from?
Two carboxylic acids
Conditions, name and reagent of acylation reactions
Name: Nucleophilic Addition - Elimination Condition: Gently heated Reagent: Nucleophiles
Acid anhydride + water ->
Carboxylic acid + carboxylic acids
Acid anhydride + alcohol ->
Ester + Carboxylic acid
Acid anhydride + ammonia ->
Primary amide + carboxylic acid
Acid anhydride + primary amide ->
Secondary amide + carboxylic acid
Evidence HCl is produced
Steamy, white fumes
Acyl chloride + water ->
Carboxylic acid + HCl
Acyl chloride + alcohol ->
Ester + HCl
Acyl chlorde + ammonia ->
Amide + Ammonium chloride
Condition and observation between acyl chloride + ammonia
Ammonia in excess White smoke from ammonium chloride
Acyl chloride + primary amide ->
Secondary amide + alkylammonium chloride salt
Conditions between acyl chloride + primary amide
Excess primary amide
Why are nucleophiles attracted to acyl chlorides in nucleophilic addition-elimination reactions
The delta positive charge on the C of the C=O bond
Mechanism of addition-elimination reactions
Nucleophile attacks C in the C=O bond. C=O bond breaks with bonding pair of electrons and transfer to the O. C-O bond reforms as C-Cl bond breaks. N-H bond breaks.
What are the multiple industrial advantages of ethanoic anhydride over ethanoyl chloride?
Less reactive so safer to handle and store. Cheaper. Does not produce toxic HCl fumes. Can be used in aspirin synthesis.
What to react to produce aspirin
Ethanoic anhydride + 2-hydroxybenzoic acid
What is the other substrate formed alongside aspirin
CH3CO2H