Chapter 5, Carbonyl Compounds (Acylation) Flashcards
What are the reagents for it?
Acyl chloride or acid anhydride
What does acylation involve?
The introduction of an acyl group on to an organic compound
What is the acyl group?
R-C=O
What is the acid anhydride group?
R-C=O
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What are the reactions of acid anhydrides and acyl chlorides when compared to one another?
Acid anhydrides are less vigorous.
Acid anhydrides also produce co-products which are not easily removed.
Why is the reaction of alcohols + acyl chlorides significant?
It is a more efficient way of preparing ester than esterification
Why is the reaction between acyl chlorides and alcohols a better way of producing esters?
Because it is a complete reaction whereas esterification is only an equilibrium
What mechanism do these compounds undergo?
Nucleophilic Addition-Elimination
Why do these compounds undergo nucleophilic attack?
The Cl or CH3COO attached to the C=O are strongly electron withdrawing so they make the C electron deficient.
The Cl- of CH3COO- groups are stable and act as good leaving groups
What are typical nucleophiles?
Water, alcohols, ammonia and amines
What is a very common product associated with these groups?
Aspirin
What method is used in the large scale production of Asprin?
Ethanoic anhydride
Why is this method used for making Asprin commercially?
Ethanoic anhydride is: Cheaper than ethanol chloride Less correlative Less susceptible to hydrolysis Less hazardous to use
What is Asprin?
Medication for pain relief
